JP2804364B2 - Process for producing oximes - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a process for producing oximes, and more particularly, to α, β-unsaturated ketones by a novel reaction carried out in the presence of a cobalt compound and an organosilicon compound. Alternatively, the present invention relates to a method for obtaining an oxime from an α, β-unsaturated nitrile and a nitrite compound.

<Prior Art> Oximes such as α-hydroxyimino ketones, α-hydroxyimino aldehydes, and α-hydroxy imino nitriles include α-diketone compounds, α-hydroxy ketone compounds, 2-amino alcohol compounds, It is useful as a synthetic intermediate for 2-diamine compounds or nitrogen-containing heterocyclic compounds such as pyrazine and triazine.

Conventionally, these oximes are prepared by reacting ketones, aldehydes or nitriles with nitrites in the presence of an acid or base,
It is produced by utilizing a reaction with α-diketones, α-ketoaldehydes or α-ketonitrile.

<Problems to be Solved by the Invention> However, since these conventional methods use an acid or a base, they cannot be applied to a compound unstable to an acid or a base, and a method using α-diketones, When asymmetric α-diketones are used, there are problems such as formation of two kinds of α-hydroxyimino ketones.

Accordingly, an object of the present invention is to provide an oxime having a specific structure from an α, β-unsaturated compound having a specific structure and a nitrite compound by a novel reaction carried out in the presence of a specific cobalt compound and an organosilicon compound. To provide an industrially feasible method for obtaining

<Means for Solving the Problems> The present invention provides a compound represented by the general formula (I): [Wherein, R ¹ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aryl group, or the following formula (a): —COOR ⁴ (a) (where R ⁴ is a carbon atom 1 to 20 alkyl groups, cycloalkyl groups or aryl groups, which may have a substituent; or the following formula (b): -CONR ⁵ R ⁶ (b) (where R ⁵ and R ^{6 May} be the same or different, and are a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group, and R ⁵ and R ⁶ may be mutually bonded to form a ring. R ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group, and R ³ is a group represented by the following formula: ^{(c): -COR 7 (c} ) ( wherein, R ⁷ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, Group or the formula represented by a is) a cycloalkyl group or an aryl group: alpha represented by a group represented by -CN], and β- unsaturated compound represented by the following general formula ^{(II): R 8 ONO (} II) [Wherein R ⁸ is an alkyl group] a nitrite compound represented by the following general formula (III): Wherein R ⁹ is an alkyl group, a cycloalkyl group, a perfluoroalkyl group or an aryl group, and R ¹⁰ is a hydrogen atom, an alkanoyl group or the following formula (d): —COOR ¹⁴ (d) (where R ¹⁴ is an alkyl group or a cycloalkyl group), and R ¹¹ is a hydrogen atom, an alkyl group,
A cycloalkyl or aryl group, R ¹² and R
¹³ may be the same or different, are a hydrogen atom or an alkyl group, may be mutually bonded to form a ring, and R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are the same or different And n may be 0 or 1.
General formula (IV): Wherein R ¹⁵ and R ¹⁶ are a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a perfluoroalkyl group, or the following formula (e): —COOR ²¹ (e) (where R ²¹ is an alkyl group Or a cycloalkyl group) or the following formula (f): -CONR ²² R ²³ (f) (where R ²² and R ²³ may be the same or different, and represent a hydrogen atom, an alkyl group, a cycloalkyl group or R ¹⁶ and R ¹⁹ are a hydrogen atom, an alkyl group, or an alkanoyl, which is an aryl group, which may have a substituent, or may be bonded to each other to form a ring. Or a group represented by the following formula (g): —COOR ²⁴ (g) (where R ²⁴ is an alkyl group or a cycloalkyl group), and R ¹⁷ and R ¹⁸ are a hydrogen atom, an alkyl group, An alkyl group or an aryl group , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹
And R ²⁰ may be the same or different from each other, and may have a substituent.] Or general formula (V): [Wherein, R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are as defined in the above general formula (IV)].
Species and general formula (VI): Wherein, R ²⁵ and R ²⁶ may be the same or different, a hydrogen atom, an alkyl group or an aryl group linear, R ²⁷
Is a hydrogen atom, a linear or branched alkyl group or an aryl group, and any one of R ²⁵ , R ²⁶ and R ²⁷ is not a hydrogen atom.] The following general formula (VII) including a step of reacting in a solvent: [Wherein, R ¹ , R ² and R ³ are as defined in the aforementioned general formula (I)].

Hereinafter, the method for producing the oximes of the present invention will be described in detail.

The α, β-unsaturated compound which is the starting material of the method of the present invention is represented by the general formula (I). In the general formula (I), R ¹ is a hydrogen atom, having 1 to 20 carbon atoms.
Or a group represented by the above formula (a) or (b). Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,
Examples thereof include n-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl.
Examples of the cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. Examples of the aryl group include a phenyl group, an α-naphthyl group, and a β-
Examples thereof include a naphthyl group, a 2-furanyl group, and a 3-furanyl group.

In the formula (a): —COOR ⁴ (a), R ⁴ is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group.
Specific examples of the cycloalkyl group and the aryl group include
The same thing can be mentioned as illustrative of those for the R ^1. Further, R ⁴ may have a substituent.

Further, in the formula (b): -CONR ⁵ R ⁶ (b), R ⁵ and R ⁶ may be the same or different and each represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group. , and the specific examples of the alkyl group and cycloalkyl group may be the same as those exemplified ones for the R ^1. Further, R ⁵ and R ⁶ may be bonded to each other to form a ring.For example, R ⁵ and R ⁶ may be bonded to each other to form a group such as a pyrrolidino group, a piperidino group, a morpholino group, and a thiomorpholino group. Is also good. In addition, R ⁵
And R ⁶ are, for example, a methyl group, an ethyl group,
It may have an alkyl group such as a propyl group and a butyl group; and an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group and a butoxy group.

R ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group.Specific examples of the alkyl group, cycloalkyl group and aryl group are the same as those exemplified for R ¹ above. Things.

R ³ is a group represented by the above formula (c): —COR ⁷ (c) or a group represented by the formula: —CN.
R ⁷ in the formula (c) is a hydrogen atom, having 1 to 20 carbon atoms.
Alkyl group, a cycloalkyl group or an aryl group, the alkyl group, specific examples of the cycloalkyl group and aryl group include the same examples of those for the R ^1.

Furthermore, in the general formula (I), R ¹ , R ² and R ³ may be the same or different, and may have a substituent.

Representative examples of the α, β-unsaturated compound represented by the general formula (I) as a starting material in the method of the present invention include 1-buten-3-one, 1-penten-3-one,
1-phenyl-2-propen-1-one, 3-decene-
2-one, 1-phenyl-1-buten-3-one, 1-
Phenyl-4,4-dimethyl-2-penten-1-one,
2-methyl-2-penten-4-one, 2-hexenal, 2-pentenenitrile and the like. They are,
The oximes which are the target substances are appropriately selected so as to obtain those having a desired structure.

In the method of the present invention, the nitrite compound to be reacted with the α, β-unsaturated compound represented by the general formula (I) is the one represented by the general formula (II). In the general formula (II), R ⁸ is an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group, a pentyl group, and a hexyl group. Can be

Nitrite ester compounds represented by the general formula (II) and typical examples include ethyl nitrite, propyl nitrite, butyl nitrite, t-butyl nitrite and the like.

In the method of the present invention, the amount of the nitrite compound represented by the general formula (II) is usually 1 to 1 with respect to the α, β-unsaturated compound represented by the general formula (I).
The equivalent is not less than equivalent, preferably 1 to 10 equivalent.

The method of the present invention relates to the method for producing α,
The β-unsaturated compound and the nitrite compound represented by the general formula (II) are combined with the general formulas (III) and (IV)
Or a method in which at least one selected from the cobalt compounds represented by (V) is reacted with the organosilicon compound represented by the general formula (VI).

In the general formula (III), R ⁹ is an alkyl group, a cycloalkyl group, a perfluoroalkyl group or an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, a t-butyl group, and the like.As the cycloalkyl group, for example, Examples include a cyclopentyl group and a cyclohexyl group. Further, examples of the perfluoroalkyl group include a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group, and examples of the aryl group include a phenyl group,
Examples include a tolyl group, an α-naphthyl group, a β-naphthyl group, a furoyl group and the like.

R ¹⁰ is a hydrogen atom, an alkanoyl group or a group represented by the following formula (d): —COOR ¹⁴ (d). Examples of the alkanoyl group for R ¹⁰ include an acetyl group, a propanoyl group, a butanoyl group, and a benzoyl group. In the formula (d), R ¹⁴ is an alkyl group or a cycloalkyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, a t-butyl group, and the like. , A cyclopentyl group, a cyclohexyl group and the like.

R ¹¹ is a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group. The alkyl group or a cycloalkyl group, for example, the same thing can be mentioned as those exemplified for the R ^14, the aryl group, for example,
Examples include a phenyl group, a tolyl group, an α-naphthyl group, a β-naphthyl group, a furoyl group and the like.

R ¹² and R ¹³ may be the same or different,
It is a hydrogen atom or an alkyl group.

Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, and a t-butyl group. Further, R ¹² and R ¹³ may be mutually bonded to form a ring, for example, mutually bonded to form a group such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. It may be.

R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ may be the same or different, may have a substituent, and n is 0 or 1. Examples of the substituent include an alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group; and an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.

In the general formula (IV), R ¹⁵ and R ²⁰ are a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a perfluoroalkyl group, or the following formula (e): —COOR ²¹ (e) or the following formula (f) : —CONR ²² R ²³ (f) Here, as the alkyl group for R ¹⁵ and R ²⁰ , for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group Group, n-pentyl group,
Examples include an n-hexyl group, and examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, and an adamantyl group.

Examples of the aryl group include a phenyl group, a tolyl group, an α-naphthyl group, a β-naphthyl group, a furoyl group and the like. Further, the aryl group may have a substituent. Examples of the perfluoroalkyl group include a trifluoromethyl group, a pentafluoroethyl group,
And a heptafluoropropyl group.

In the formula (e), R ²¹ is an alkyl group or a cycloalkyl group, and examples of the alkyl group include:
Methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, t
-Butyl group and the like, and as the cycloalkyl group,
For example, a cyclopentyl group, a cyclohexyl group and the like can be mentioned.

Further, in the formula (f), R ²² and R ²³ may be the same or different and are a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and are the same as R ⁵ and R ^{6 in} the formula (b). And may have a substituent.

R ¹⁶ and R ¹⁹ are a hydrogen atom, an alkyl group, an alkanoyl group or a group represented by the following formula (g): —COOR ²⁴ (g). Examples of the alkyl group for R ¹⁶ and R ¹⁹ include a methyl group, an ethyl group, an n-propyl group,
iso-propyl group, n-butyl group, sec-butyl group, t-
Examples include a butyl group and the like, and examples of the alkanoyl group include an acetyl group, a propanoyl group, a butanoyl group, and a benzoyl group. Also, in equation (g), R
²⁴ is an alkyl group or a cycloalkyl group, for example, the same as those exemplified for R ^{21 in the} formula (e).

R ¹⁷ and R ¹⁸ are a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group.
For R ⁵ and R ⁶ include exemplary ones and the same.

R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ may be the same or different from each other, and may have a substituent. Examples of the substituent include an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group and a t-butyl group; Ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, alkoxy group such as t-butoxy group; halogen atom such as fluorine, chlorine, bromine, iodine, etc. Is mentioned.

In the general formula (V), R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are as defined in the general formula (IV).

Representative examples of the cobalt compound represented by the general formula (III) include those represented by the following formula.

Further, as a typical example of the cobalt compound represented by the general formula (IV) or (V), a cobalt (II) complex represented by a general formula: CoL ₂ having a ligand L shown in Table 1 below is exemplified. Is done.

In the method of the present invention, the compound represented by the general formula (III) or (IV)
Alternatively, the cobalt compound represented by (V) may be used alone or in combination of two or more.

In the method of the present invention, the amount of the cobalt compound used is preferably about 1 to 20 mol%, more preferably about 5 to 20 mol%, based on the α, β-unsaturated compound represented by the general formula (I). Is good.

In the method of the present invention, the reaction is carried out in the presence of the organosilicon compound represented by the general formula (VI) together with the cobalt compound. In the general formula (VI) representing this organosilicon compound, R ²⁵ and R ²⁶ may be the same or different and are a hydrogen atom, a linear alkyl group or an aryl group, and R ²⁷ is a hydrogen atom, a linear or branched Alkyl group or aryl group. Examples of the linear alkyl group include a methyl group, an ethyl group, and an n-
Examples include a propyl group and an n-butyl group, and examples of the branched alkyl group include an iso-propyl group, an iso-butyl group, a sec-butyl group, and a t-butyl group.
Examples of the aryl group include a phenyl group, a tolyl group, an α-naphthyl group, and a β-naphthyl group.

Any one of R ²⁵ , R ²⁶ and R ²⁷ is not a hydrogen atom.

Representative examples of the organosilicon compound represented by the general formula (VI) include dimethylphenylsilane, triethylsilane, diethylsilane, diphenylsilane, phenylsilane and the like.

In the method of the present invention, the organosilicon compound represented by the general formula (VI) is generally used in an amount of 1 equivalent or more with respect to the α, β-unsaturated compound represented by the general formula (1). is there.

The reaction solvent is not particularly limited as long as it is other than water. For example, aliphatic or alicyclic hydrocarbon solvents such as pentane, hexane, heptane, cyclopentane, cyclohexane, octane, nonane, decane, cycloheptane and cyclooctane; benzene,
Aromatic hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane, 1,2-dichloroethane, 1,1-dichloroethane, chloroform and carbon tetrachloride; cyanides such as acetonitrile, propionitrile and butyronitrile Hydrocarbon solvents; ketone solvents such as acetone, methyl ethyl ketone, diethyl ketone, cyclohexanone and cyclopentanone; ether solvents such as tetrahydrofuran, diethyl ether, dimethoxyethane and dioxane; ethanol, ethanol, 2-propanol and 2-methyl Alcohol solvents such as -2-propanol; and ester solvents such as methyl acetate and ethyl acetate. These may be used alone or in combination of two or more. The amount of the reaction solvent used is generally about 5 ml per 1 mmol of the α, β-unsaturated compound represented by the general formula (I).

In the method of the present invention, the reaction temperature is usually from 0 to 100.
C., and the reaction time is usually about 1 to 100 hours.

The reaction may be performed in an inert atmosphere such as nitrogen or argon.

The reaction may be performed batchwise or continuously in the liquid phase.

Representative examples of the oximes represented by the general formula (VII) obtained by the method of the present invention include, for example, 3-hydroxyimino-2-butanone, 2-hydroxyimino-3-pentanone, 2-hydroxyimino −
1-phenyl-1-propanone, 3-hydroxyimino-2-decanone, 1-phenyl-2-hydroxyimino-3-butanone, 1-phenyl-2-hydroxyimino-4,4-dimethyl-1-pentanone, 2 -Methyl-3-
Oxymes obtained by the method of the present invention include, for example, α-hydroxyimino-4-pentanone, 2-hydroxyiminohexanal, and 2-hydroxyiminopentanenitrile.
It is useful as a synthetic intermediate such as a hydroxyketone compound, a 2-aminoalcohol compound, a 1,2-diamine compound, or a nitrogen-containing heterocyclic compound such as pyrazine and triazine.

<Examples> Hereinafter, the present invention will be described specifically with reference to examples of the present invention, but the present invention is not limited to these examples.

(Examples 1 to 8) In each example, 0.5 mmol of an α, β-unsaturated compound and N, N′-bis (2-ethoxycarbonyl-3-oxobutylidene) ethylenediaminatocobalt shown in Table 2 were added to a reaction vessel. (II) 20 mg (0.05 mmol) of the complex and 2.5 ml of tetrahydrofuran were charged, and the inside of the reaction vessel was replaced with argon. Next, n-butyl nitrite and phenyl silane are
An amount corresponding to the equivalent ratio (molar ratio) shown in Table 2 was added to the α, β-unsaturated compound, and the mixture was added at room temperature (Examples 1-4, 7-8) or at 60 ° C. (Examples 5-6). The reaction was performed for the time shown in FIG. After completion of the reaction, 1.5 ml of methanol and 0.1 ml of concentrated hydrochloric acid were added, and the mixture was stirred at room temperature for 30 minutes. Next, 20 ml of water was added, and a saturated aqueous solution of sodium hydrogen carbonate was added to neutralize hydrochloric acid.
Extracted with dichloromethane.

The organic layer was washed with saturated saline, and dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, dichloromethane was distilled off under reduced pressure, and the residue was purified by thin-layer chromatography to obtain a reaction product shown in Table 2. The yield of the reaction product was measured. Table 2 shows the results.

<Effects of the Invention> According to the method of the present invention, α, β- is obtained by a novel reaction carried out in the presence of a cobalt compound and an organosilicon compound.
Oximes such as α-hydroxyimino ketones, α-hydroxyiminoaldehydes, and α-hydroxyimino nitriles can be obtained from unsaturated ketones or α, β-unsaturated nitriles and nitrite compounds. . The resulting oximes are α-diketone compounds, α-
It is useful as a synthetic intermediate such as a hydroxyketone compound, a 2-aminoalcohol compound, a 1,2-diamine compound, or a nitrogen-containing heterocyclic compound such as pyrazine and triazine.

Continuation of the front page (51) Int.Cl. ⁶ identification code FI B01J 31/22 B01J 31/22 X C07B 61/00 300 C07B 61/00 300 (58) Investigated field (Int.Cl. ⁶ , DB name) C07C 249/06 C07C 251/36 C07C 255/64 C07C 253/30 REGISTRY (STN) CA (STN)

Claims (1)

(57) [Claims] 1. A compound of the general formula (I): [Wherein, R ¹ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aryl group, or the following formula (a): —COOR ⁴ (a) (where R ⁴ is a carbon atom 1 to 20 alkyl groups, cycloalkyl groups or aryl groups, which may have a substituent; or the following formula (b): -CONR ⁵ R ⁶ (b) (where R ⁵ and R ^{6 May} be the same or different, and are a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group, and R ⁵ and R ⁶ may be mutually bonded to form a ring. R ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or an aryl group, and R ³ is a group represented by the following formula: ^{(c): -COR 7 (c} ) ( wherein, R ⁷ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, Group or the formula represented by a is) a cycloalkyl group or an aryl group: alpha represented by a group represented by -CN], and β- unsaturated compound represented by the following general formula ^{(II): R 8 ONO (} II) [Wherein R ⁸ is an alkyl group] a nitrite compound represented by the following general formula (III): Wherein R ⁹ is an alkyl group, a cycloalkyl group, a perfluoroalkyl group or an aryl group, and R ¹⁰ is a hydrogen atom, an alkanoyl group or the following formula (d): —COOR ¹⁴ (d) (where R ¹⁴ is an alkyl group or a cycloalkyl group), and R ¹¹ is a hydrogen atom, an alkyl group,
A cycloalkyl or aryl group, R ¹² and R
¹³ may be the same or different, are a hydrogen atom or an alkyl group, may be mutually bonded to form a ring, and R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are the same or different And n may be 0 or 1.
General formula (IV): Wherein R ¹⁵ and R ¹⁶ are a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a perfluoroalkyl group, or the following formula (e): —COOR ²¹ (e) (where R ²¹ is an alkyl group Or a cycloalkyl group) or the following formula (f): -CONR ²² R ²³ (f) (where R ²² and R ²³ may be the same or different, and represent a hydrogen atom, an alkyl group, a cycloalkyl group or R ¹⁶ and R ¹⁹ are a hydrogen atom, an alkyl group, or an alkanoyl, which is an aryl group, which may have a substituent, or may be bonded to each other to form a ring. Or a group represented by the following formula (g): —COOR ²⁴ (g) (where R ²⁴ is an alkyl group or a cycloalkyl group), and R ¹⁷ and R ¹⁸ are a hydrogen atom, an alkyl group, An alkyl group or an aryl group , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹
And R ²⁰ may be the same or different from each other, and may have a substituent.] Or general formula (V): [Wherein, R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are as defined in the above general formula (IV)].
Species and general formula (VI): Wherein, R ²⁵ and R ²⁶ may be the same or different, a hydrogen atom, an alkyl group or an aryl group linear, R ²⁷
Is a hydrogen atom, a linear or branched alkyl group or an aryl group, and any one of R ²⁵ , R ²⁶ and R ²⁷ is not a hydrogen atom.] The following general formula (VII) including a step of reacting in a solvent: [Wherein, R ¹ , R ² and R ³ are as defined in the above general formula (I)].