JP6933835B2 - Method for producing alkoxysilane by hydrosilylation reaction of carbonyl compound using iron complex catalyst - Google Patents

Description

The present invention relates to a method for producing an alkoxysilane, and more particularly to a method for producing an alkoxysilane by a hydrosilylation reaction of a carbonyl compound using an iron complex catalyst.

Alkoxysilanes are useful compounds as various synthetic reaction intermediates and as monomers for inducing organic silane polymers.
Alkoxysilanes are synthesized by the hydrosilylation reaction of carbonyl compounds such as ketones with hydrosilanes, which require a transition metal complex catalyst. The hydrosilylation reaction of a carbonyl compound is widely used as an atom economy reaction that does not produce a by-product, and as a reaction for reducing a carbonyl group and protecting an alcohol group in one step.
Conventionally, complexes of noble metals such as ruthenium and rhodium have been used as catalysts, but these noble metals are expensive, and toxicity due to contamination with trace metals in products has become a problem. Therefore, there is a need to develop a catalytic reaction using a metal that is inexpensive and has extremely low toxicity. So far, complexes of manganese, iron, cobalt, and nickel have been reported as base metal complexes that exhibit catalytic activity in the hydrosilylation reaction of carbonyl compounds (see Non-Patent Documents 1 to 4), but all of them have reaction conditions and reactions. There are problems in terms of selectivity and catalytic activity.

T. K. Mukhopadhay, M.M. Flores, T.M. L. Groy, R.M. J. Trovic, J. et al. Am. Chem. Soc. , 2014, 136 (3), 882-885. A. M. Tondreau, E.I. Lobkovsky, P.M. J. Chirik, Org. Lett. , 2008, 10 (13), 2789-2792. Q. Niu, H.M. Sun, X. Li, H. -F. Klein, U.S.A. Florke, Organometallics, 2013, 32 (18), 5235-5238. L. P. Beeter, M. et al. Henrion, L. Brelot, C.I. Darcel, M.D. J. Checti, J. et al. -B. Sortais, V.I. Rittleng, Adv. Synth. Catal. , 2012, 354, 2619-2624.

An object of the present invention is to provide a method for producing an alkoxysilane, which can efficiently produce an alkoxysilane.

As a result of diligent studies to solve the above problems, the present inventors hydrosilylate a carbonyl compound by using a specific iron complex having an iminobipyridine derivative as a ligand as a catalyst together with a reducing agent. As a result, it was found that the alkoxysilane can be efficiently produced, and the present invention has been completed.

（式（Ａ）中、Ｒ¹及びＲ²はそれぞれ独立して炭素原子数１〜６の炭化水素基を、Ｒ³は
水素原子、又はハロゲン原子を含んでいてもよい炭素原子数１〜１０の炭化水素基を、Ｒ⁴は水素原子、又は炭素原子数１〜２０の炭化水素基を、Ｘはそれぞれ独立してハロゲン
原子を、ｉは０〜４の整数を、ｊは０〜３の整数を表す。但し、ｉが２〜４の整数である場合、Ｒ¹の炭化水素基同士が連結して環状構造を形成していてもよく、ｊが２又は３で
ある場合、Ｒ²の炭化水素基同士が連結して環状構造を形成していてもよい。）
＜２＞ 前記カルボニル化合物が、下記式（Ｉ）で表されるカルボニル化合物である、＜
１＞に記載のアルコキシシランの製造方法。

（式（Ｉ）中、Ｒはそれぞれ独立してヘテロ原子を含んでいてもよい炭素原子数１〜２０の炭化水素基、ヘテロ原子を含んでいてもよい炭素原子数１〜２０のアルコキシ基、又は水素原子を表す。）
＜３＞ 前記ヒドロシランが、下記式（ＩＩ−１）〜（ＩＩ−３）の何れかで表されるヒ
ドロシランである、＜１＞又は＜２＞に記載のアルコキシシランの製造方法。

（式（ＩＩ−１）〜（ＩＩ−２）中、Ｒ’はそれぞれ独立してハロゲン原子を含んでいてもよい炭素原子数１〜２０の炭化水素基を表す。） That is, the present invention is as follows.
<1> A method for producing an alkoxysilane, which comprises a hydrosilylation step of reacting a carbonyl compound with a hydrosilane in the presence of a catalyst to produce an alkoxysilane.
A method for producing an alkoxysilane, which comprises using an iron complex represented by the following formula (A) and a reducing agent as the catalyst.

(In the formula (A), R ¹ and R ² each independently contain a hydrocarbon group having 1 to 6 carbon atoms, and R ³ may contain a hydrogen atom or a halogen atom having 1 to 10 carbon atoms. R ⁴ is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, X is an independent halogen atom, i is an integer of 0 to 4, and j is 0 to 3. It represents an integer. However, when i is an integer of 2 to 4, ^{the hydrocarbon groups of R 1} may be connected to each other to form a cyclic structure, and when j is 2 or 3, R ² of Hydrocarbon groups may be connected to each other to form a cyclic structure.)
<2> The carbonyl compound is a carbonyl compound represented by the following formula (I), <
1> The method for producing an alkoxysilane.

(In the formula (I), R is a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a hetero atom, and an alkoxy group having 1 to 20 carbon atoms which may contain a hetero atom. Or represents a hydrogen atom.)
<3> The method for producing an alkoxysilane according to <1> or <2>, wherein the hydrosilane is a hydrosilane represented by any of the following formulas (II-1) to (II-3).

(In formulas (II-1) to (II-2), R'represents a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a halogen atom.)

According to the present invention, an alkoxysilane can be efficiently produced.

In explaining the present invention, specific examples will be given, but the contents are not limited to the following as long as the gist of the present invention is not deviated, and the present invention can be appropriately modified.

（式（Ａ）中、Ｒ¹及びＲ²はそれぞれ独立して炭素原子数１〜６の炭化水素基を、Ｒ³は
水素原子、又はハロゲン原子を含んでいてもよい炭素原子数１〜１０の炭化水素基を、Ｒ⁴は水素原子、又は炭素原子数１〜２０の炭化水素基を、Ｘはそれぞれ独立してハロゲン
原子を、ｉは０〜４の整数を、ｊは０〜３の整数を表す。但し、ｉが２〜４の整数である場合、Ｒ¹の炭化水素基同士が連結して環状構造を形成していてもよく、ｊが２又は３で
ある場合、Ｒ²の炭化水素基同士が連結して環状構造を形成していてもよい。）
本発明者らは、「式（Ａ）で表される鉄錯体」と「還元剤」を反応系中に添加することによって容易に活性種を誘導することができ、これがカルボニル化合物のヒドロシリル化反応において高い触媒活性を示して、アルコキシシランを効率よく製造することができることを見出したのである。かかる反応は、安価で入手し易く、毒性が極めて低い鉄の錯体を利用して、比較的温和な条件で進行させることができる優れた特長を有している。
なお、本発明における「カルボニル化合物」は、カルボニル基（＞Ｃ＝Ｏ）を少なくとも１つ有する有機化合物を、「ヒドロシラン」とは、ケイ素−水素結合（Ｓｉ−Ｈ）を少なくとも１つ有する化合物を、「アルコキシシラン」とは、ケイ素原子に結合したアルコキシ基（Ｓｉ−ＯＲ）を少なくとも１つ有する化合物を意味するものとする。
従って、「カルボニル化合物」と「ヒドロシラン」の反応として、例えば下記反応式で示されるような反応が挙げられる（「カルボニル化合物」が「２−オクタノン」であり、「ヒドロシラン」がジフェニルシランである。）。即ち、「ヒドロシラン」は、ケイ素−水素結合（Ｓｉ−Ｈ）を２つ以上有するものであってもよく、また「ヒドロシリル化工程」は、１分子の「ヒドロシラン」によって、１分子の「カルボニル化合物」をヒドロシリル化するものであっても、１分子の「ヒドロシラン」によって、２分子以上の「カルボニル化合物」をヒドロシリル化するものであってもよい。

また、「還元剤」は、「式（Ａ）で表される鉄錯体」の鉄原子を還元する単体又は化合物を意味するものとする。式（Ａ）で表される鉄錯体の鉄原子の形式酸化数は２＋であるため、Ｆｅ（２＋）をＦｅ（０）に還元できる単体又は化合物が、本発明における「還元剤」に該当する。例えばメチルリチウム（ＭｅＬｉ）を式（Ａ）で表される鉄錯体（ＬＦｅＸ₂（Ｌ：イミノビピリジン配位子））と共に使用した場合、ＭｅＬｉとＬＦｅＸ₂が反応してＬＦｅＭｅ₂が生成し、２つのＭｅ基が還元的脱離してＬＦｅが生成するものと推
測される。
以下、「ヒドロシリル化工程」について詳細に説明する。 <Manufacturing method of alkoxysilane>
The method for producing an alkoxysilane, which is one aspect of the present invention, is abbreviated as a hydrosilylation step (hereinafter, abbreviated as "hydrosilylation step") in which a "carbonyl compound" and a "hydrosilane" are reacted in the presence of a catalyst to produce an "alkoxysilane". In some cases), the method comprises the use of the following "iron complex represented by the formula (A)" and "reducing agent" as the catalyst.

(In the formula (A), R ¹ and R ² each independently contain a hydrocarbon group having 1 to 6 carbon atoms, and R ³ may contain a hydrogen atom or a halogen atom having 1 to 10 carbon atoms. R ⁴ is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, X is an independent halogen atom, i is an integer of 0 to 4, and j is 0 to 3. It represents an integer. However, when i is an integer of 2 to 4, ^{the hydrocarbon groups of R 1} may be connected to each other to form a cyclic structure, and when j is 2 or 3, R ² of Hydrocarbon groups may be connected to each other to form a cyclic structure.)
The present inventors can easily induce an active species by adding an "iron complex represented by the formula (A)" and a "reducing agent" to the reaction system, which is a hydrosilylation reaction of a carbonyl compound. It was found that the alkoxysilane can be efficiently produced by showing high catalytic activity in the above. Such a reaction has an excellent feature that it can proceed under relatively mild conditions by utilizing an iron complex which is inexpensive, easily available, and has extremely low toxicity.
The "carbonyl compound" in the present invention is an organic compound having at least one carbonyl group (> C = O), and the "hydrosilane" is a compound having at least one silicon-hydrogen bond (Si—H). , "Alkoxysilane" shall mean a compound having at least one alkoxy group (Si-OR) bonded to a silicon atom.
Therefore, examples of the reaction between the "carbonyl compound" and the "hydrosilane" include reactions as shown by the following reaction formulas (the "carbonyl compound" is "2-octanone" and the "hydrosilane" is diphenylsilane. ). That is, the "hydrosilane" may have two or more silicon-hydrogen bonds (Si—H), and the “hydrosilylation step” involves one molecule of “hydrosilane” and one molecule of “carbonyl compound”. , Or two or more molecules of "carbonyl compound" may be hydrosilylated by one molecule of "hydrosilane".

Further, the "reducing agent" shall mean a simple substance or a compound that reduces an iron atom of the "iron complex represented by the formula (A)". Since the formal oxidation number of the iron atom of the iron complex represented by the formula (A) is 2+, a simple substance or a compound capable of reducing Fe (2+) to Fe (0) corresponds to the "reducing agent" in the present invention. .. For example, when methyllithium (MeLi) is _{used together with an iron complex (LFeX 2} (L: iminobipyridine ligand)) represented by the formula (A), MeLi and LFEX ₂ react to _{generate LFeMe 2} and 2 It is presumed that one Me group is reductively eliminated to produce LFe.
Hereinafter, the "hydrosilylation step" will be described in detail.

式（Ａ）中のＲ¹及びＲ²は、それぞれ独立して「炭素原子数１〜６の炭化水素基」を表しているが、「炭化水素基」は、分岐構造、環状構造のそれぞれを有していてもよく、飽和炭化水素基、芳香族炭化水素基等の何れであってもよいものとする。なお、「芳香族炭化水素基」には、フェニル基のような芳香族性を有する単環の芳香族炭化水素基が含まれるほか、ナフチル基のような芳香族性を有する多環の芳香族炭化水素基も含まれるものとする。
Ｒ¹、Ｒ²の炭化水素基の炭素原子数としては、好ましくは５以下、より好ましくは４以下であり、Ｒ¹、Ｒ²が芳香族炭化水素基である場合の炭素原子数は、通常６である。
Ｒ¹、Ｒ²としては、メチル基（−ＣＨ₃，−Ｍｅ）、エチル基（−Ｃ₂Ｈ₅，−Ｅｔ）、
ｎ−プロピル基（−ⁿＣ₃Ｈ₇，−ⁿＰｒ）、ｉ−プロピル基（−ⁱＣ₃Ｈ₇，−ⁱＰｒ）、ｎ−
ブチル基（−ⁿＣ₄Ｈ₉，−ⁿＢｕ）、ｔ−ブチル基（−^tＣ₄Ｈ₉，−^tＢｕ）、ｎ−ペンチル基（−ⁿＣ₅Ｈ₁₁）、ｎ−ヘキシル基（−ⁿＣ₆Ｈ₁₃，−ⁿＨｅｘ）、シクロヘキシル基（−^cＣ₆Ｈ₁₁，−Ｃｙ）、フェニル基（−Ｃ₆Ｈ₅，−Ｐｈ）等が挙げられる。
なお、「ｉが２〜４の整数である場合、Ｒ¹の炭化水素基同士が連結して環状構造を形
成していてもよく、ｊが２又は３である場合、Ｒ²の炭化水素基同士が連結して環状構造
を形成していてもよい」が、炭化水素基同士が連結して環状構造を形成している構造として、下記式で表されるものが挙げられる。

The hydrosilylation step is a step of using an "iron complex represented by the formula (A)" and a "reducing agent" as catalysts, but the specific type of the "iron complex represented by the formula (A)" is , Is not particularly limited, and can be appropriately selected depending on the purpose. The "iron complex represented by the formula (A)" used in the hydrosilylation step is not limited to one type, and two or more types may be used in combination. Hereinafter, the "iron complex represented by the formula (A)" will be described in detail.

^{R 1} and R ² in the formula (A) independently represent "hydrocarbon groups having 1 to 6 carbon atoms", but "hydrocarbon groups" have a branched structure and a cyclic structure, respectively. It may have any of a saturated hydrocarbon group, an aromatic hydrocarbon group, and the like. The "aromatic hydrocarbon group" includes a monocyclic aromatic hydrocarbon group having an aromatic property such as a phenyl group, and a polycyclic aromatic group having an aromatic property such as a naphthyl group. Hydrocarbon groups shall also be included.
The ^{number of carbon atoms of the hydrocarbon groups of R 1} and R ² is preferably 5 or less, more preferably 4 or less, and the ^{number of carbon atoms when R 1} and R ² are aromatic hydrocarbon groups is usually 5 or less. It is 6.
Examples of R ¹ and R ² include methyl group (-CH ₃ , -Me), ethyl group (-C ₂ H ₅ , -Et), and
n-propyl group ( ^-n C ₃ H ₇ , ^-n Pr), i-propyl group ( ^-i C ₃ H ₇ , ^-i Pr), n-
Butyl group ( ^-n C ₄ H ₉ , ^-n Bu), t-butyl group ( ^-t C ₄ H ₉ , ^-t Bu), n-pentyl group ( ^-n C ₅ H ₁₁ ), n-hexyl group (-n C 5 H 11) _{^{- n C 6 H 13, -}} n Hex), cyclohexyl _{^{(- c C 6 H 11,}} -Cy), phenyl group (-C ₆ H _5, -Ph), and the like.
In addition, "when i is an integer of 2 to 4, ^{the hydrocarbon groups of R 1} may be connected to each other to form a cyclic structure, and when j is 2 or 3, the hydrocarbon group of ^{R 2 may be formed.} They may be connected to each other to form a cyclic structure. ”However, examples of the structure in which hydrocarbon groups are connected to each other to form a cyclic structure include those represented by the following formulas.

^{R 3} in the formula (A) represents a "hydrocarbon atom" or a "hydrocarbon group having 1 to 10 carbon atoms which may contain a halogen atom", and the "hydrocarbon group" is R ^1. Etc., and "may contain a halogen atom" means that the hydrogen atom of the "hydrocarbon group" may be substituted with a halogen atom.
When R ³ is a hydrocarbon group, the number of carbon atoms of the hydrocarbon group is preferably 6 or less.
It is more preferably 4 or less, still more preferably 3 or less.
R ³ includes hydrogen atom (-H), methyl group (-CH ₃ , -Me), trifluoromethyl group (-CF ₃ ), ethyl group (-C ₂ H ₅ , -Et), n-propyl group. ( ^-N C ₃ H ₇ , ^-n Pr
), I-propyl group ( ^-i C ₃ H ₇ , ^-i Pr), n- butyl group ( ^-n C ₄ H ₉ , ^-n Bu), t-butyl group ( ^-t C ₄ H ₉ , ^-t Bu) and the like can be mentioned, but a hydrogen atom, a methyl group, a trifluoromethyl group and a t-butyl group are preferable.

^{R 4} in the formula (A) represents "hydrocarbon atom" or "hydrocarbon group having 1 to 10 carbon atoms", but "hydrocarbon group" is synonymous with the case ^{of R 1 and the like.} ..
When R ⁴ is a hydrocarbon group, the number of carbon atoms of the hydrocarbon group is preferably 18 or less, more preferably 16 or less, still more preferably 14 or less, and when R ⁴ is an aromatic hydrocarbon group. The number of carbon atoms in is usually 6 or more.
R ⁴ includes hydrogen atom, methyl group, phenyl group, 2,6-
Examples thereof include a dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,4,6-trimethylphenyl group and a 2,6-diisopropylphenyl group.

Although X in the formula (A) independently represents a "halogen atom", a chlorine atom (-Cl), a bromine atom (-Br), and an iodine atom (-I) are preferable, and a bromine atom is particularly preferable. preferable. When it is a bromine atom, alkoxysilane can be produced in a higher yield.

The iron complex represented by the formula (A) is a complex having an iminobipyridine derivative as a ligand, and examples of the iminobipyridine derivative include those represented by the following formula.

Examples of the iron complex represented by the formula (A) include those represented by the following formula.

なお、かかる合成経路の具体的反応条件等は、Ｒ．Ｇ．Ｈｉｃｋｓ，Ｏｒｇ．Ｌｅｔｔ．２００４，６，１８８７．、Ｇ．Ｖｅｒｎｉｅｓｔ，Ｊ．Ｏｒｇ．Ｃｈｅｍ．２０１０，７５，４２４．、Ｕ．Ｓｃｈｕｂｅｒｔ，Ｏｒｇ．Ｌｅｔｔ．２０００，２，３３７３．、Ｙ．Ｄ．Ｍ．Ｃｈａｍｐｏｕｒｅｔ，Ｎｅｗ Ｊ．Ｃｈｅｍ．２００７，３１，７５．、Ｍ．Ｂ．Ｄｉａｚ−Ｖａｌｅｎｚｕｅｌａ，Ｃｈｅｍ．Ｅｕｒ．Ｊ．，２００９，１５，１２２７．、Ｃ．Ｒａｎｇｈｅａｒｄ，Ｄａｌｔｏｎ Ｔｒａｎｓ．，２００９，７７０．、Ｘ．Ｄａｉ，Ａｄｖ．Ｓｙｎｔｈ．Ｃａｔａｌ．，２０１４，３５６，１３１７．等を参考にすることができる。
また、例えば下記式で表される化合物等は、市販されており、原料として利用して幅広いイミノビピリジン誘導体を調製することが可能である。

The method for preparing the iminobipyridine derivative is not particularly limited, and it can be produced by appropriately combining known organic synthesis methods, and it may be produced by a synthetic route represented by the following formula.

The specific reaction conditions of such a synthetic route are described in R. et al. G. Hicks, Org. Lett. 2004, 6, 1887. , G. Verniest, J. et al. Org. Chem. 2010, 75, 424. , U. Schubert, Org. Lett. 2000, 2,3373. , Y. D. M. Champouret, New J. et al. Chem. 2007, 31, 75. , M.M. B. Diaz-Valenzuela, Chem. Euro. J. , 2009, 15, 1227. , C.I. Rangeard, Dalton Trans. , 2009, 770. , X. Dai, Adv. Synth. Catal. , 2014, 356, 1317. Etc. can be referred to.
Further, for example, compounds represented by the following formulas are commercially available, and a wide range of iminobipyridine derivatives can be prepared by using them as raw materials.

The method for preparing the iron complex represented by the formula (A) is not particularly limited, but usually includes reacting an iminobipyridine derivative with a divalent iron halide.

The amount of the "iron complex represented by the formula (A)" used in the hydrosilylation step can be appropriately selected depending on the intended purpose, but it is usually converted into the amount of substance with respect to the amount of "hydrosilane" used, which will be described later. 0.01 mol% or more, preferably 0.05 mol% or more, more preferably 0.1 mol% or more, usually 5.0 mol% or less, preferably 3.0 mol% or less, more preferably 1.0 mol% or less. .. Within the above range, alkoxysilane can be produced in a higher yield.

The hydrosilylation step is a step of using an "iron complex represented by the formula (A)" and a "reducing agent" as catalysts, but the specific type of the "reducing agent" is not particularly limited and is known. Those can be appropriately selected according to the purpose. The "reducing agent" used in the hydrosilylation step is not limited to one type, and two or more types may be used in combination. Hereinafter, the "reducing agent" will be described in detail.
As the reducing agent, lithium borohydride (LiBH ₄ ) and sodium borohydride (N)
aBH ₄ ), sodium cyanoborohydride (NaBH ₃ CN), lithium triethylborohydride (LiBHEt ₃ ), sodium triethylborohydride (NaBHEt ₃ ), lithium hydride tri (sec-butyl) boron lithium (LiBH (sec-sec-)) Bu) ₃ ), sodium borohydride such as tri (sec-butyl) boron borohydride (KBH (sec-Bu) ₃ ); lithium aluminum hydride (LiAlH ₄ ), bis hydride (2-methoxyethoxy) Examples thereof include hydride complexes of aluminum such as sodium aluminum (NaAlH ₂ (OC ₂ H ₄ OCH ₃ ) _2). Of these, sodium borohydride (NaBHEt ₃ ) is particularly preferable.
As other reducing agents, alkyllithium reagents such as methyllithium, ethyllithium and butyllithium can also be used.

The amount of the "reducing agent" used in the hydrosilylation step can be appropriately selected depending on the purpose, but it is usually 2 in terms of the amount of substance used with respect to the amount of the "iron complex represented by the formula (A)". Equivalent or more, preferably 3 equivalents or more, more preferably 4 equivalents or more, usually 10 equivalents or less, preferably 8 equivalents or less, more preferably 6 equivalents or less. Within the above range, alkoxysilane can be produced in a higher yield.

（式（Ｉ）中、Ｒはそれぞれ独立してヘテロ原子を含んでいてもよい炭素原子数１〜２０の炭化水素基、ヘテロ原子を含んでいてもよい炭素原子数１〜２０のアルコキシ基、又は水素原子を表す。）
式（Ｉ）中のＲは、それぞれ独立して「ヘテロ原子を含んでいてもよい炭素原子数１〜２０の炭化水素基」、「ヘテロ原子を含んでいてもよい炭素原子数１〜２０のアルコキシ基」、又は「水素原子」を表しているが、「炭化水素基」は、分岐構造、環状構造、炭素−炭素不飽和結合のそれぞれを有していてもよく、飽和炭化水素基、不飽和炭化水素基、芳香族炭化水素基等の何れであってもよいものとする。また、「ヘテロ原子を含んでいてもよい」とは、炭化水素基の水素原子がヘテロ原子、即ち、窒素原子、酸素原子、硫黄原子、ハロゲン原子等を含む１価の官能基で置換されていてもよいほか、炭化水素基の炭素骨格内部の炭素原子が窒素原子、酸素原子、硫黄原子、ハロゲン原子等を含む２価以上の官能基（連結基）で置換されていてもよいことを意味する。
Ｒが炭化水素基である場合の炭化水素基の炭素原子数としては、好ましくは１２以下、より好ましくは１０以下であり、Ｒが芳香族炭化水素基である場合の炭素原子数は、通常６以上である。
Ｒに含まれる官能基や連結基としては、エーテル基（オキサ基，−Ｏ−）、チオエーテル基（チア基，−Ｓ−）、フルオロ基（−Ｆ）、クロロ基（−Ｃｌ）、ブロモ基（−Ｂｒ）、ヨード基（−Ｉ）等が挙げられる。
Ｒとしては、メチル基（−ＣＨ₃，−Ｍｅ）、エチル基（−Ｃ₂Ｈ₅，−Ｅｔ）、ｎ−プ
ロピル基（−ⁿＣ₃Ｈ₇，−ⁿＰｒ）、ｉ−プロピル基（−ⁱＣ₃Ｈ₇，−ⁱＰｒ）、ｎ−ブチル基（−ⁿＣ₄Ｈ₉，−ⁿＢｕ）、ｔ−ブチル基（−^tＣ₄Ｈ₉，−^tＢｕ）、３−ブテニル基（−ＣＨ₂ＣＨ₂ＣＨ＝ＣＨ₂）、ｎ−ペンチル基（−ⁿＣ₅Ｈ₁₁）、ｎ−ヘキシル基（−ⁿＣ₆Ｈ₁₃，−ⁿＨｅｘ）、ｎ−ヘプチル基（−ⁿＣ₇Ｈ₁₅，−ⁿＨｅｐ）、ｎ−オクチル基（−ⁿＣ₈
Ｈ₁₇，−ⁿＯｃｔ）、シクロヘキシル基（−^cＣ₆Ｈ₁₁，−Ｃｙ）、フェニル基（−Ｃ₆Ｈ₅
，−Ｐｈ）、メトキシ基（−ＯＣＨ₃，−ＯＭｅ）、エトキシ基（−ＯＣ₂Ｈ₅，−ＯＥｔ
）、ｎ−プロポキシ基（−ＯⁿＣ₃Ｈ₇，−ＯⁿＰｒ）、ｉ−プロポキシ基（−ＯⁱＣ₃Ｈ₇，
−ＯⁱＰｒ）、ｎ−ブトキシ基（−ＯⁿＣ₄Ｈ₉，−ＯⁿＢｕ）、ｔ−ブトキシ基（−Ｏ^tＣ₄
Ｈ₉，−Ｏ^tＢｕ）、ｎ−ペントキシ基（−ＯⁿＣ₅Ｈ₁₁）、フェノキシ基（−ＯＣ₆Ｈ₅，−ＯＰｈ）、水素原子（−Ｈ）等が挙げられる。
カルボニル化合物としては、下記式で表されるものが挙げられる。

The hydrosilylation step is a step of reacting a "carbonyl compound" and a "hydrosilane" in the presence of a catalyst to produce an "alkoxysilane", but the specific type of the "carbonyl compound" is not particularly limited and is intended for the purpose. A carbonyl compound represented by the following formula (I) can be mentioned, which can be appropriately selected depending on the situation. The "carbonyl compound" used in the hydrosilylation step is not limited to one type, and two or more types may be used in combination. Hereinafter, the "carbonyl compound represented by the formula (I)" will be described in detail.

(In the formula (I), R is a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a hetero atom, and an alkoxy group having 1 to 20 carbon atoms which may contain a hetero atom. Or represents a hydrogen atom.)
R in the formula (I) are independently "hydrocarbon groups having 1 to 20 carbon atoms which may contain heteroatoms" and "hydrocarbon groups having 1 to 20 carbon atoms which may contain heteroatoms", respectively. Although it represents an "alkoxy group" or a "hydrocarbon atom", the "hydrocarbon group" may have a branched structure, a cyclic structure, or a carbon-carbon unsaturated bond, respectively, and is a saturated hydrocarbon group or an unsaturated bond. It may be either a saturated hydrocarbon group or an aromatic hydrocarbon group. Further, "may contain a hetero atom" means that the hydrogen atom of the hydrocarbon group is replaced with a hetero atom, that is, a monovalent functional group containing a nitrogen atom, an oxygen atom, a sulfur atom, a halogen atom and the like. In addition, it means that the carbon atom inside the carbon skeleton of the hydrocarbon group may be substituted with a divalent or higher functional group (linking group) including a nitrogen atom, an oxygen atom, a sulfur atom, a halogen atom and the like. do.
The number of carbon atoms of the hydrocarbon group when R is a hydrocarbon group is preferably 12 or less, more preferably 10 or less, and the number of carbon atoms when R is an aromatic hydrocarbon group is usually 6. That is all.
Examples of the functional group and linking group contained in R include an ether group (oxa group, -O-), a thioether group (thia group, -S-), a fluoro group (-F), a chloro group (-Cl), and a bromo group. (-Br), iodo group (-I) and the like can be mentioned.
R includes methyl group (-CH ₃ , -Me), ethyl group (-C ₂ H ₅ , -Et), n-propyl group ( ^-n C ₃ H ₇ , ^-n Pr), and i-propyl group (-n C 3 H 7, -n Pr). − ^I C ₃ H ₇ , − ⁱ Pr), n − butyl group (− ⁿ C ₄ H ₉ , − ⁿ Bu), t − butyl group (− ^t C ₄ H ₉ , − ^t Bu), 3-butenyl group (-CH ₂ CH ₂ CH = CH ₂ ), n-pentyl group ( ^-n C ₅ H ₁₁ ), n-hexyl group ( ^-n C ₆ H ₁₃ , ^-n Hex), n-heptyl group ( ^-n C) ₇ H ₁₅ , − ⁿ Hep), n − octyl group (− ⁿ C ₈₎
H ₁₇ , ^-n Oct), cyclohexyl group ( ^-c C ₆ H ₁₁ , -Cy), phenyl group (-C ₆ H ₅₎
, -Ph), methoxy group (-OCH ₃ , -OME), ethoxy group (-OC ₂ H ₅ , -OEt)
), N-propoxy group ^{_{(-O n C 3 H 7,}} -O n Pr), i- propoxy group (-O ⁱ C ₃ H _7,
-O ⁱ Pr), n- butoxy group ^{_{(-O n C 4 H 9,}} -O n Bu), t- butoxy (-O ^t C _{4
^{H 9, -O t Bu),}} n- pentoxy group ^{_{(-O n C 5 H 11)}} , a phenoxy group _{(-OC 6 H 5, -OPh)} , include hydrogen atom (-H) or the like.
Examples of the carbonyl compound include those represented by the following formulas.

The amount of the "carbonyl compound" used in the hydrosilylation step can be appropriately selected depending on the intended purpose, but is usually 0.5 equivalents or more, preferably 1 equivalent, in terms of substance amount with respect to the amount of "hydrosilane" used. As mentioned above, it is more preferably 2 equivalents or more, usually 10 equivalents or less, preferably 5 equivalents or less, and more preferably 3 equivalents or less. Within the above range, alkoxysilane can be produced in a higher yield.

（式（ＩＩ−１）〜（ＩＩ−２）中、Ｒ’はそれぞれ独立してハロゲン原子を含んでいてもよい炭素原子数１〜２０の炭化水素基を表す。）
式（ＩＩ−１）〜（ＩＩ−２）中のＲ’は、それぞれ独立して「ハロゲン原子を含んでいてもよい炭素原子数１〜２０の炭化水素基」を表しているが、「炭化水素基」は、分岐構造、環状構造、炭素−炭素不飽和結合のそれぞれを有していてもよく、飽和炭化水素基、不飽和炭化水素基、芳香族炭化水素基等の何れであってもよいものとする。また、「ハロゲン原子を含んでいてもよい」とは、「炭化水素基」の水素原子がハロゲン原子に置換されていてもよいことを意味する。
Ｒ’の炭化水素基の炭素原子数としては、好ましくは１２以下、より好ましくは１０以下であり、Ｒが芳香族炭化水素基である場合の炭素原子数は、通常６以上である。
Ｒ’としては、メチル基（−ＣＨ₃，−Ｍｅ）、エチル基（−Ｃ₂Ｈ₅，−Ｅｔ）、ｎ−
プロピル基（−ⁿＣ₃Ｈ₇，−ⁿＰｒ）、ｉ−プロピル基（−ⁱＣ₃Ｈ₇，−ⁱＰｒ）、ｎ−ブチル基（−ⁿＣ₄Ｈ₉，−ⁿＢｕ）、ｔ−ブチル基（−^tＣ₄Ｈ₉，−^tＢｕ）、ｎ−ペンチル基（−ⁿＣ₅Ｈ₁₁）、ｎ−ヘキシル基（−ⁿＣ₆Ｈ₁₃，−ⁿＨｅｘ）、ｎ−ヘプチル基（−ⁿＣ₇Ｈ₁₅，−ⁿＨｅｐ）、ｎ−オクチル基（−ⁿＣ₈Ｈ₁₇，−ⁿＯｃｔ）、シクロヘキシル基（−^cＣ
₆Ｈ₁₁，−Ｃｙ）、フェニル基（−Ｃ₆Ｈ₅，−Ｐｈ）、等が挙げられる。
ヒドロシランとしては、下記式で表されるものが挙げられる。

The specific type of "hydrosilane" used in the hydrosilylation step is not particularly limited and may be appropriately selected depending on the intended purpose, but is represented by any of the following formulas (II-1) to (II-3). Hydrosilane to be used. The "hydrosilane" used in the hydrosilylation step is not limited to one type, and two or more types may be used in combination. Hereinafter, "hydrosilane represented by any of the formulas (II-1) to (II-3)" will be described in detail.

(In formulas (II-1) to (II-2), R'represents a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a halogen atom.)
R'in formulas (II-1) to (II-2) independently represent "hydrocarbon groups having 1 to 20 carbon atoms which may contain halogen atoms", but "hydrocarbons" The "hydrocarbon group" may have a branched structure, a cyclic structure, or a carbon-carbon unsaturated bond, and may be any of a saturated hydrocarbon group, an unsaturated hydrocarbon group, an aromatic hydrocarbon group, and the like. It should be good. Further, "may contain a halogen atom" means that the hydrogen atom of the "hydrocarbon group" may be replaced with a halogen atom.
The number of carbon atoms of the hydrocarbon group of R'is preferably 12 or less, more preferably 10 or less, and the number of carbon atoms when R is an aromatic hydrocarbon group is usually 6 or more.
As R', methyl group (-CH ₃ , -Me), ethyl group (-C ₂ H ₅ , -Et), n-
Propyl group ( ^-n C ₃ H ₇ , ^-n Pr), i-propyl group ( ^-i C ₃ H ₇ , ^-i Pr), n- butyl group ( ^-n C ₄ H ₉ , ^-n Bu), t -Butyl group ( ^-t C ₄ H ₉ , ^-t Bu), n-pentyl group ( ^-n C ₅ H ₁₁ ), n-hexyl group ( ^-n C ₆ H ₁₃ , ^-n Hex), n-heptyl group ^{_{(- n C 7 H 15,}} - n Hep), n- octyl group ^{_{(- n C 8 H 17,}} - n Oct), cyclohexyl (- ^c C
₆ H _11, -Cy), phenyl group _{(-C 6 H 5, -Ph)} , and the like.
Examples of the hydrosilane include those represented by the following formula.

The hydrosilylation step may or may not use a solvent.
When a solvent is used, the specific type of the solvent is not particularly limited, but hydrocarbon solvents such as hexane, benzene and toluene, ether solvents such as diethyl ether, 1,4-dioxane and tetrahydrofuran (THF) and the like can be used. Can be mentioned.

The reaction conditions such as the reaction temperature and reaction time of the hydrosilylation step are not particularly limited, but specific examples will be described below.
The reaction temperature is usually 0 ° C. or higher, preferably 10 ° C. or higher, more preferably 15 ° C. or higher, and usually 100 ° C. or lower, preferably 50 ° C. or lower, more preferably 20 ° C. or lower.
The reaction time is usually 0.5 hours or more, preferably 1 hour or more, more preferably 2 hours or more, usually 48 hours or less, preferably 24 hours or less, more preferably 12 hours or less, still more preferably 3 hours or less. Is.
The hydrosilylation step is usually preferably carried out in an inert atmosphere such as nitrogen or argon.
Within the above range, alkoxysilane can be produced in a higher yield.

（式（ＩＩＩ−１）〜（ＩＩＩ−６）中、Ｒはそれぞれ独立してヘテロ原子を含んでいてもよい炭素原子数１〜２０の炭化水素基、ヘテロ原子を含んでいてもよい炭素原子数１〜２０のアルコキシ基、又は水素原子を、Ｒ’はそれぞれ独立してハロゲン原子を含んでいてもよい炭素原子数１〜２０の炭化水素基を表す。）
なお、Ｒ、Ｒ’は、「式（Ｉ）で表されるカルボニル化合物」及び「式（ＩＩ−１）〜（ＩＩ−３）の何れかで表されるヒドロシラン」の場合と同様である。 The specific type of "alkoxysilane" produced by the hydrosilylation step is not particularly limited and may be appropriately selected depending on the production purpose, but any of the following formulas (III-1) to (III-6). Examples thereof include an alkoxysilane represented by.

(In formulas (III-1) to (III-6), R is a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a hetero atom, and a carbon atom which may contain a hetero atom. An alkoxy group having a number of 1 to 20 or a hydrogen atom, and R'representing a hydrocarbon group having a carbon atom number of 1 to 20 which may independently contain a halogen atom.)
R and R'are the same as in the case of "carbonyl compound represented by formula (I)" and "hydrosilane represented by any of formulas (II-1) to (II-3)".

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention can be appropriately modified as long as it does not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed in a limited manner by the specific examples shown below.

<Preparation of iron complex represented by formula (A)>
The iron complexes shown in Tables 1 and 2 were prepared by the same method as described in WO 2016/208554.

<Manufacturing of alkoxysilane>
(Example 1)
Precisely weigh the iron complex (3.0 mg, 0.0058 mmol) of Table 1 1a into a Schlenk tube into which nitrogen gas has flowed in, add 2-octanone (0.93 mL, 5.8 mmol), and start stirring at room temperature. bottom. After adding diphenylsilane (1.1 mL, 5.8 mmol) to this solution, a toluene solution of 1 M sodium borohydride (120 μL, 0.1)
When 2 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction products were quantified by the absolute calibration curve method, it was confirmed that the following 2a and 2b alkoxysilanes were produced. The results are shown in Table 3.

(Example 2)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1b in Table 1. The results are shown in Table 3.

(Example 3)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1c in Table 1. The results are shown in Table 3.

(Example 4)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1d in Table 1. The results are shown in Table 3.

(Example 5)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1e in Table 1. The results are shown in Table 3.

(Example 6)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1f in Table 1. The results are shown in Table 3.

(Example 7)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1 g in Table 2. The results are shown in Table 3.

(Example 8)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1h in Table 2. The results are shown in Table 3.

(Example 9)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1i in Table 2. The results are shown in Table 3.

(Example 10)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1j in Table 2. The results are shown in Table 3.

(Example 11)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1k in Table 2. The results are shown in Table 3.

(Example 12)
The reaction was carried out in the same manner as in Example 1 except that the iron complex was changed to 1 l in Table 2. The results are shown in Table 3.

(Example 13)
The iron complex (3.0 mg, 0.0054 mmol) of Table 1 1c was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, 2-octanone was added, and stirring was started at room temperature. When diphenylsilane was added to this solution and then a toluene solution of 1M hydrogenated triethylboron sodium (110 μL, 0.11 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. 2-Octanone and diphenylsilane were used in the substance amount ratios shown in Table 4. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction products were quantified by the absolute calibration curve method, it was confirmed that the following 2a and 2b alkoxysilanes were produced. The results are shown in Table 4.

(Example 14)
The reaction was carried out in the same manner as in Example 13 except that the substance amount ratio of 2-octanone and diphenylsilane was changed to that shown in Table 4. The results are shown in Table 4.

(Example 15)
The reaction was carried out in the same manner as in Example 13 except that the substance amount ratio of 2-octanone and diphenylsilane was changed to that shown in Table 4. The results are shown in Table 4.

(Example 16)
The reaction was carried out in the same manner as in Example 13 except that the substance amount ratio of 2-octanone and diphenylsilane was changed to that shown in Table 4. The results are shown in Table 4.

(Example 17)
The iron complex (3.0 mg, 0.0058 mmol) of Table 1 1a was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, 2-octanone (19 mL, 120 mmol) was added, and stirring was started at room temperature. When diphenylsilane (11 mL, 58 mmol) was added to this solution and then a toluene solution of 1 M hydrogenated triethylboron sodium (120 μL, 0.12 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction products were quantified by the absolute calibration curve method, it was confirmed that the following 2a and 2b alkoxysilanes were produced. The results are shown in Table 5.

(Example 18)
The reaction was carried out in the same manner as in Example 17 except that the iron complex was changed to 1b in Table 1. The results are shown in Table 5.

(Example 19)
The reaction was carried out in the same manner as in Example 17 except that the iron complex was changed to 1c in Table 1. The results are shown in Table 5.

(Example 20)
The reaction was carried out in the same manner as in Example 17 except that the iron complex was changed to 1d in Table 1. The results are shown in Table 5.

(Example 21)
The reaction was carried out in the same manner as in Example 17 except that the iron complex was changed to 1 g in Table 2. The results are shown in Table 5.

(Example 22)
The reaction was carried out in the same manner as in Example 17 except that the iron complex was changed to 1k in Table 2. The results are shown in Table 5.

(Example 23)
The reaction was carried out in the same manner as in Example 19 except that the reaction time was changed to that shown in Table 5. The results are shown in Table 5.

(Example 24)
The reaction was carried out in the same manner as in Example 19 except that the amount of the iron complex used and the reaction time were changed to those shown in Table 5. The results are shown in Table 5.

(Example 25)
The iron complex (3.0 mg, 0.0054 mmol) of Table 1 1c was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, 2-octanone (2.6 mL, 16 mmol) was added, and stirring was started at room temperature. When phenylsilane (0.68 mL, 5.4 mmol) was added to this solution and then a toluene solution of 1 M hydrogenated triethylboron sodium (110 μL, 0.11 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. Changed. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction product was quantified by the absolute calibration curve method, it was confirmed that the alkoxysilane represented by the following formula was produced (yield: 70%).

(Example 26)
The iron complex (3.0 mg, 0.0054 mmol) of Table 1 1c was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, 2-octanone (1.7 mL, 11 mmol) was added, and stirring was started at room temperature. After adding phenyl (methyl) silane (0.74 mL, 5.4 mmol) to this solution, a toluene solution of 1 M hydrogenated triethylboron sodium (110 μL, 0.11 mmol) was added, and the reaction solution changed from a brown solution to a light brown solution. It turned into a color solution. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction product was quantified by the absolute calibration curve method, it was confirmed that the alkoxysilane represented by the following formula was produced (yield: 78%).

(Example 27)
The iron complex (5.0 mg, 0.0089 mmol) of Table 1 1c was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, 2-octanone (10 mL, 65 mmol) was added, and stirring was started at room temperature. Then, 1 mL of this solution was transferred to a Schlenk tube in which nitrogen gas flowed in, and 2-octanone (1.9 mL, 18 mmol), diphenylsilane (1.7 mL, 8.9 mmol), and 1 M sodium triethyl hydride were added to this solution. Toluene solution (18 μL, 0.0018 mmol) was added in this order. The reaction solution changed from a brown solution to a light brown solution. This state was used as the reaction start, and after 2 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction products were quantified by the absolute calibration curve method, it was confirmed that the following 2a and 2b alkoxysilanes were produced. The results are shown in Table 6.

(Example 28)
The reaction was carried out in the same manner as in Example 27, except that the amount of sodium borohydride (reducing agent) used was changed to that shown in Table 6. The results are shown in Table 6.

(Example 29)
The reaction was carried out in the same manner as in Example 27, except that the amount of the iron complex used and the amount of sodium borohydride (reducing agent) used were changed to those shown in Table 6. The results are shown in Table 6.

(Example 30)
The reaction was carried out in the same manner as in Example 27, except that the amount of the iron complex used and the amount of sodium borohydride (reducing agent) used were changed to those shown in Table 6. The results are shown in Table 6.

(Example 31)
The reaction was carried out in the same manner as in Example 27, except that the amount of the iron complex used was changed to that shown in Table 6. The results are shown in Table 6.

(Example 32)
The reaction was carried out in the same manner as in Example 27, except that the amount of the iron complex used and the amount of sodium borohydride (reducing agent) used were changed to those shown in Table 6. The results are shown in Table 6.

(Example 33)
The reaction was carried out in the same manner as in Example 27, except that the amount of the iron complex used, the amount of sodium borohydride (reducing agent) used, and the reaction time were changed to those shown in Table 6. The results are shown in Table 6.

(Example 34)
The reaction was carried out in the same manner as in Example 27, except that the amount of the iron complex used, the amount of sodium borohydride (reducing agent) used, and the reaction time were changed to those shown in Table 6. The results are shown in Table 6.

(Example 35)
Precisely weigh the iron complex (3.0 mg, 0.0054 mmol) of Table 1 1c into a Schlenk tube into which nitrogen gas has flowed, add 5-hexene-2-one (1.3 mL, 11 mmol), and stir at room temperature. Started. When diphenylsilane (1.0 mL, 5.4 mmol) was added to this solution and then a toluene solution of 1 M hydrogenated triethylboron sodium (110 μL, 0.11 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. Changed. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction product was quantified by the absolute calibration curve method, it was confirmed that the alkoxysilane represented by the following formula was produced (yield: 67%).

(Example 36)
The iron complex (3.0 mg, 0.0054 mmol) of Table 1 1c was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, n-octanal (1.7 mL, 11 mmol) was added, and stirring was started at room temperature. When diphenylsilane (1.0 mL, 5.4 mmol) was added to this solution and then a toluene solution of 1 M hydrogenated triethylboron sodium (110 μL, 0.11 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. Changed. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction product was quantified by the absolute calibration curve method, it was confirmed that the alkoxysilane represented by the following formula was produced (yield: 54%).

(Example 37)
The iron complex (3.0 mg, 0.0054 mmol) of Table 1 1c was precisely weighed into a Schlenk tube into which nitrogen gas had flowed in, heptyl acetate (1.6 mL, 11 mmol) was added, and stirring was started at room temperature. When diphenylsilane (1.0 mL, 5.4 mmol) was added to this solution and then a toluene solution of 1 M hydrogenated triethylboron sodium (110 μL, 0.11 mmol) was added, the reaction solution changed from a brown solution to a light brown solution. Changed. This state was regarded as the start of the reaction, and after 24 hours, the reaction solution was analyzed by high performance liquid chromatography (199 nm). When the reaction product was quantified by the absolute calibration curve method, it was confirmed that the alkoxysilane represented by the following formula was produced (yield: 64%).

The alkoxysilane produced by the method for producing an alkoxysilane of the present invention can be used as a raw material for a silicone resin, a silane compound, a silylating agent, silica and the like.

Claims (3)

A method for producing an alkoxysilane, which comprises a hydrosilylation step of reacting a carbonyl compound with a hydrosilane in the presence of a catalyst to produce an alkoxysilane.
A method for producing an alkoxysilane, which comprises using an iron complex represented by the following formula (A) and a reducing agent as the catalyst.

(In the formula (A), R ¹ and R ² each independently contain a hydrocarbon group having 1 to 6 carbon atoms, and R ³ may contain a hydrogen atom or a halogen atom having 1 to 10 carbon atoms. R ⁴ is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, X is an independent halogen atom, i is an integer of 0 to 4, and j is 0 to 3. It represents an integer. However, when i is an integer of 2 to 4, ^{the hydrocarbon groups of R 1} may be connected to each other to form a cyclic structure, and when j is 2 or 3, R ² of Hydrocarbon groups may be connected to each other to form a cyclic structure.) The method for producing an alkoxysilane according to claim 1, wherein the carbonyl compound is a carbonyl compound represented by the following formula (I).

(In the formula (I), R is a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a hetero atom, and an alkoxy group having 1 to 20 carbon atoms which may contain a hetero atom. Or represents a hydrogen atom.) The method for producing an alkoxysilane according to claim 1 or 2, wherein the hydrosilane is a hydrosilane represented by any of the following formulas (II-1) to (II-3).

(In formulas (II-1) to (II-2), R'represents a hydrocarbon group having 1 to 20 carbon atoms which may independently contain a halogen atom.)