JPS6244543B2 - - Google Patents
Info
- Publication number
- JPS6244543B2 JPS6244543B2 JP3071080A JP3071080A JPS6244543B2 JP S6244543 B2 JPS6244543 B2 JP S6244543B2 JP 3071080 A JP3071080 A JP 3071080A JP 3071080 A JP3071080 A JP 3071080A JP S6244543 B2 JPS6244543 B2 JP S6244543B2
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- alkyl group
- formula
- palladium
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 2-oxo-5-vinylcyclopentanecarboxylic acid ester Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- RHSSQVDHAKRQNF-UHFFFAOYSA-N methyl 2-ethenyl-5-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1C(C=C)CCC1=O RHSSQVDHAKRQNF-UHFFFAOYSA-N 0.000 claims description 3
- YBZVVZXGGAAUTO-UHFFFAOYSA-N methyl 3-oxo-8-phenoxyoct-6-enoate Chemical compound COC(=O)CC(=O)CCC=CCOc1ccccc1 YBZVVZXGGAAUTO-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000002941 palladium compounds Chemical class 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UAXNXOMKCGKNCI-UHFFFAOYSA-N 1-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 UAXNXOMKCGKNCI-UHFFFAOYSA-N 0.000 description 1
- OFABFBIDKPPPFB-UHFFFAOYSA-N 3-oxooct-6-enoic acid Chemical class CC=CCCC(=O)CC(O)=O OFABFBIDKPPPFB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ODLYPKCMHCNDFX-UHFFFAOYSA-N OC(CC(CCC=CCOC1=CC=CC=C1)=O)=O Chemical compound OC(CC(CCC=CCOC1=CC=CC=C1)=O)=O ODLYPKCMHCNDFX-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は医薬，香料などの合成用の中間体とし
て有用な２―オキソ―５―ビニルシクロペンタン
カルボン酸エステル及びその１―置換体の製造方
法に関するものである。
近年、金属錯体を用いる化学は著しい進歩をと
げ、とくにπ―アリル錯体を経る炭素―炭素結合
の形成など多くの新しい反応が見い出されてい
る。これらの反応は特に環状のラクトン及びケト
ンの合成に有益に利用できる。しかし、これらの
環化反応はこれ迄は主として大環状の形成にのみ
有用であるとされていて、５員環、６員環化合物
の合成には応用されていなかつた。
本発明者はパラジウム系触媒を用い活性メチレ
ン基とアリル型エーテルとの分子内反応による５
員環ケトンの合成につき鋭意研究を重ねた結果本
発明に到達したものである。
而して、本発明は３―オキソ―６―オクテン酸
エステル又はその２―置換体を溶媒中において、
パラジウム化合物とホスフイン化合物とからなる
触媒を用いて加熱環化することによる２―オキソ
―５―ビニルシクロペンタンカルボン酸エステル
又はその１―置換体の製造方法に係わるものであ
る。
本発明の化合物を製造するための原料化合物で
ある構造式
（ここで、Ｒはアルキル基、R′は水素又はア
ルキル基、R″はアルキル基又は芳香族基を示
す）
で表わされる３―オキソ―６―オクテン酸エステ
ル（）はアセト酢酸エステルのジアニオンと１
―クロロ―２―ブテンの４―R″O置換体との反応
によつて容易に得ることができる。本発明は下記
反応式で示される如く、前記化合物（）を溶媒
中においてパラジウム化合物とホスフイン化合物
とからなる触媒を用いて加熱環化し、２―オキソ
―５―ビニルシクロペンタンカルボン酸エステル
又はその１―アルキル置換体（）とするもので
ある。本反応においては２―オキソ―５―シクロ
ヘプテンカルボン酸エステル又はその１―アルキ
ル置換体（）が副生物として生成する。しか
し、この生成量は触媒と溶媒との組合せを適宜選
択することにより減少させることが可能であり、
特に３―オキソ―６―オクテン酸エステルの２―
アルキル置換体を原料として用いた場合には、主
として本発明の目的とする５員環ケトンが生成す
る。
なお、上記式中のＲはアルキル基，R′は水素
又はアルキル基，R″はアルキル基又は芳香族基
を示し、ここでいうアルキル基はフエニル基で一
部置換されたアルキル基であつてもよく、炭素鎖
中に不飽和二重結合又は不飽和三重結合を含むア
ルキル基であつてもよいことは発明の本質から明
らかであろう。
本発明の反応においては、パラジウム化合物と
ホスフイン化合物とからなる触媒が用いられる。
パラジウム化合物としては酢酸パラジウム、パラ
ジウムアセチルアセトナート、硝酸パラジウム、
硫酸パラジウム、塩化パラジウム等、またホスフ
イン化合物としてはトリブチルホスフイン
（PBu3）、トリフエニルホスフイン（PPh3）、ビス
（ジフエニルホスフイノ）エタン（DIPHOS）等
が使用できる。なお、硝酸パラジウム、塩化パラ
ジウムなどの塩を使用するときは酢酸カリウム、
ナトリウムアルコラート、三級アミンなどの塩基
を共存させることが望ましい。触媒量は原料化合
物である３―オキソ―６―オクテン酸エステル
（）に対して、パラジウム化合物0.5乃至20モル
％、ホスフイン化合物１乃至40モル％の割合で使
用される。
また、本発明の反応は溶媒中において加熱する
ことにより実施される。溶媒としては、三級ブチ
ルアルコール、ジオキサン、アセトン、テトラヒ
ドロフラン、ベンゼン、キシレン、アセトニトリ
ル、プロピオニトリルなど本発明の反応を妨害し
ないものであればいずれも用いることができる
が、特にアセトニトリル、プロピオニトリルなど
の有機シアノ化合物を溶媒として用い溶媒の沸点
まで加熱し還流下に反応させる態様を実施すれ
ば、本発明の目的とする化合物（）が収率よく
得られる。
本発明の方法に従つて得られる化合物は種々の
有用な化合物の合成、特に医薬、香料などの中間
体として用いられる。例えば、香料として使用さ
れているジヒドロジヤスモン酸メチルエステル
（）は下記反応で示される如く、１―ペンチル
―２―オキソ―５―ビニルシクロペンタンカルボ
ン酸メチル（）をヨウ化ナトリウムで脱カルボ
メトキシ化し、得られた２―ペンチル―３―ビニ
ルシクロペンタノン（）をハイドロボレーシヨ
ンしてジオールとし、これを酸化してケト酸と
し、次いでジアゾメタンでメチル化することによ
り得ることができる。
次に、実施例により本発明を具体的に設明す
る。
実施例 １
還流冷却器を備えたフラスコ中に３―オキソ―
８―フエノキシ―６―オクテン酸メチル0.1モル
と溶媒としてのアセトニトリルを入れ、次いで酢
酸パラジウム0.01モルとトリフエニルホスフイン
0.05モルとからなる触媒を加え溶媒の沸点まで加
熱し還流下に１時間反応させた。反応終了後、常
法に従つて減圧蒸留することにより、65〜70℃／
２mmＨｇ留分として２―オキソ―５―ビニルシク
ロペンタンカルボン酸メチルが59％の収率で得ら
れた。
この留分が２―オキソ―５―ビニルシクロペン
タンカルボン酸メチルであることは下記の分析結
果から確認された。
赤外スペクトル分析（フイルム）
1756，1722cm-1（Ｃ＝Ｏ）
1647cm-1（Ｃ＝Ｃ）
NMR（CCl4）スペクトル分析
δ1.10〜2.70（ｍ，5H）
2.74〜3.30（ｍ，1H）
3.62 （ｓ，3H）
4.79〜5.18（ｍ，2H）
5.36〜6.00（ｍ，1H）
実施例 ２
還流冷却器を備えたフラスコ中に表に示す如き
３―オキソ―８―フエノキシ―６―オクテン酸メ
チルの２―置換体（R′）0.1モルと溶媒を入れ、
次いで酢酸パラジウム0.01モルとホスフイン化合
物0.05モルとからなる触媒を加え溶媒の沸点まで
加熱し還流下に所定時間反応させた。反応終了
後、ガスクロマトグラフイーで測定した生成物の
収率を表に示した。またカツコ内には常法に従つ
て減圧蒸留して得た分離収率を示した。
The present invention relates to a method for producing 2-oxo-5-vinylcyclopentanecarboxylic acid ester and its 1-substituted product, which are useful as intermediates for the synthesis of pharmaceuticals, fragrances, etc. In recent years, chemistry using metal complexes has made remarkable progress, and many new reactions have been discovered, particularly the formation of carbon-carbon bonds via π-allyl complexes. These reactions can be particularly advantageously used in the synthesis of cyclic lactones and ketones. However, until now, these cyclization reactions have been thought to be mainly useful only for forming macrocycles, and have not been applied to the synthesis of 5- and 6-membered ring compounds. The present inventor has developed a method using a palladium-based catalyst to generate 5
The present invention was achieved as a result of extensive research into the synthesis of membered ring ketones. Therefore, the present invention provides 3-oxo-6-octenoic acid ester or its 2-substituted product in a solvent,
This invention relates to a method for producing 2-oxo-5-vinylcyclopentanecarboxylic acid ester or its 1-substituted product by thermal cyclization using a catalyst consisting of a palladium compound and a phosphine compound. Structural formula that is a raw material compound for producing the compound of the present invention (Here, R is an alkyl group, R′ is hydrogen or an alkyl group, and R″ is an alkyl group or an aromatic group.) 1
It can be easily obtained by the reaction of -chloro-2-butene with a 4-R″O substituted product.As shown in the reaction formula below, the present invention involves the reaction of the above compound () with a palladium compound and a phosphine in a solvent. 2-oxo-5-vinylcyclopentanecarboxylic acid ester or its 1-alkyl substituted product () is obtained by heating cyclization using a catalyst consisting of a compound.In this reaction, 2-oxo-5-cyclo Heptene carboxylic acid ester or its 1-alkyl substituted product () is produced as a by-product.However, the amount produced can be reduced by appropriately selecting the combination of catalyst and solvent.
In particular, 2- of 3-oxo-6-octenoic acid esters
When an alkyl substituted product is used as a raw material, a five-membered ring ketone, which is the object of the present invention, is mainly produced. In addition, in the above formula, R is an alkyl group, R' is hydrogen or an alkyl group, and R'' is an alkyl group or an aromatic group, and the alkyl group here is an alkyl group partially substituted with a phenyl group. It is clear from the nature of the invention that it may be an alkyl group containing an unsaturated double bond or an unsaturated triple bond in the carbon chain.In the reaction of the present invention, a palladium compound and a phosphine compound A catalyst consisting of is used.
Palladium compounds include palladium acetate, palladium acetylacetonate, palladium nitrate,
Palladium sulfate, palladium chloride, etc., and as phosphine compounds, tributylphosphine (PBu 3 ), triphenylphosphine (PPh 3 ), bis(diphenylphosphino)ethane (DIPHOS), etc. can be used. When using salts such as palladium nitrate and palladium chloride, use potassium acetate,
It is desirable to coexist a base such as sodium alcoholate or tertiary amine. The amount of catalyst used is 0.5 to 20 mol % of the palladium compound and 1 to 40 mol % of the phosphine compound, based on the raw material compound 3-oxo-6-octenoic acid ester (). Moreover, the reaction of the present invention is carried out by heating in a solvent. As the solvent, any solvent can be used as long as it does not interfere with the reaction of the present invention, such as tertiary butyl alcohol, dioxane, acetone, tetrahydrofuran, benzene, xylene, acetonitrile, propionitrile, etc. In particular, acetonitrile, propionitrile By using an organic cyano compound such as the following as a solvent, heating it to the boiling point of the solvent, and reacting under reflux, the compound () targeted by the present invention can be obtained in good yield. The compounds obtained according to the method of the present invention are used in the synthesis of various useful compounds, particularly as intermediates for pharmaceuticals, fragrances, and the like. For example, dihydrodiasmonic acid methyl ester (), which is used as a fragrance, is produced by decarbomethoxylating methyl 1-pentyl-2-oxo-5-vinylcyclopentanecarboxylate () with sodium iodide, as shown in the reaction below. The resulting 2-pentyl-3-vinylcyclopentanone (2) is hydroborated to give a diol, oxidized to give a keto acid, and then methylated with diazomethane. Next, the present invention will be concretely established through examples. Example 1 3-oxo- in a flask equipped with a reflux condenser
Add 0.1 mole of methyl 8-phenoxy-6-octenoate and acetonitrile as a solvent, then add 0.01 mole of palladium acetate and triphenylphosphine.
A catalyst consisting of 0.05 mol was added, heated to the boiling point of the solvent, and reacted under reflux for 1 hour. After the reaction is completed, the temperature is reduced to 65-70°C by distillation under reduced pressure according to a conventional method.
Methyl 2-oxo-5-vinylcyclopentanecarboxylate was obtained as a 2 mmHg fraction with a yield of 59%. It was confirmed from the analysis results below that this fraction was methyl 2-oxo-5-vinylcyclopentanecarboxylate. Infrared spectrum analysis (film) 1756, 1722cm -1 (C=O) 1647cm -1 (C=C) NMR (CCl 4 ) spectrum analysis δ1.10-2.70 (m, 5H) 2.74-3.30 (m, 1H) 3.62 (s, 3H) 4.79-5.18 (m, 2H) 5.36-6.00 (m, 1H) Example 2 3-oxo-8-phenoxy-6-octenoic acid as shown in the table in a flask equipped with a reflux condenser. Add 0.1 mole of 2-substituted methyl (R′) and a solvent,
Next, a catalyst consisting of 0.01 mol of palladium acetate and 0.05 mol of a phosphine compound was added, heated to the boiling point of the solvent, and reacted under reflux for a predetermined time. After the reaction was completed, the yield of the product measured by gas chromatography is shown in the table. In addition, the separation yield obtained by vacuum distillation according to a conventional method is shown in the box.
【表】【table】
【表】【table】
Claims (1)
キル基，R″はアルキル基又は芳香族基を示す） で表わされる３―オキソ―６―オクテン酸エステ
ルを溶媒中においてパラジウム化合物とホスフイ
ン化合物とからなる触媒を用いて加熱環化するこ
とを特徴とする構造式 （式中、Ｒはアルキル基、R′は水素又はアル
キル基を示す） で表わされる２―オキソ―５―ビニルシクロペン
タンカルボン酸エステルの製造方法。 ２ 前項記載の３―オキソ―６―オクテン酸エス
テルを有機シアノ化合物溶媒中において、酢酸パ
ラジウムとトリフエニルホスフインとからなる触
媒を用いて加熱還流下に環化する特許請求の範囲
第１項記載の製造方法。 ３ ３―オキソ―８―フエノキシ―６―オクテン
酸メチルを環化して２―オキソ―５―ビニルシク
ロペンタンカルボン酸メチルとする特許請求の範
囲第１項又は第２項記載の製造方法。[Claims] 1. Structural formula (In the formula, R is an alkyl group, R' is hydrogen or an alkyl group, and R'' is an alkyl group or an aromatic group). A structural formula characterized by thermal cyclization using a catalyst consisting of (In the formula, R is an alkyl group, and R' is hydrogen or an alkyl group.) A method for producing a 2-oxo-5-vinylcyclopentanecarboxylic acid ester represented by the formula: 2. Claim 1, wherein the 3-oxo-6-octenoic acid ester described in the preceding paragraph is cyclized under heating under reflux in an organic cyano compound solvent using a catalyst consisting of palladium acetate and triphenylphosphine. manufacturing method. 3. The manufacturing method according to claim 1 or 2, wherein methyl 3-oxo-8-phenoxy-6-octenoate is cyclized to produce methyl 2-oxo-5-vinylcyclopentanecarboxylate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3071080A JPS56127334A (en) | 1980-03-11 | 1980-03-11 | Preparation of 2-oxo-5-vinylcyclopentanecarboxylic ester and its 1-alkyl substitution product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3071080A JPS56127334A (en) | 1980-03-11 | 1980-03-11 | Preparation of 2-oxo-5-vinylcyclopentanecarboxylic ester and its 1-alkyl substitution product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56127334A JPS56127334A (en) | 1981-10-06 |
| JPS6244543B2 true JPS6244543B2 (en) | 1987-09-21 |
Family
ID=12311197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3071080A Granted JPS56127334A (en) | 1980-03-11 | 1980-03-11 | Preparation of 2-oxo-5-vinylcyclopentanecarboxylic ester and its 1-alkyl substitution product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56127334A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63268097A (en) * | 1987-04-27 | 1988-11-04 | Tokyo Keiso Kk | Signal transmission equipment |
-
1980
- 1980-03-11 JP JP3071080A patent/JPS56127334A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63268097A (en) * | 1987-04-27 | 1988-11-04 | Tokyo Keiso Kk | Signal transmission equipment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56127334A (en) | 1981-10-06 |
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