Title:
（７Ｅ）−７，９−デカジエン酸エステルの製造方法。
Document Type and Number:
Japanese Patent JP6826018
Kind Code:
B2
Abstract:
One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R 3 O (R 2 O) CHCH=CH (CH 2 ) 5 CO 2 R 1 , to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar 3 P=CH 2 , to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).
Inventors:
Hiroki Miyake
Tsuyoshi Kanao
Ryo Komatsu
Tsuyoshi Kanao
Ryo Komatsu
Application Number:
JP2017195641A
Publication Date:
February 03, 2021
Filing Date:
October 06, 2017
Export Citation:
Assignee:
Shin-Etsu Chemical Co., Ltd.
International Classes:
C07C67/343; C07C67/03; C07C67/32; C07C69/587; C07C69/73
Domestic Patent References:
| JP2169546A | ||||
| JP2014218497A | ||||
| JP2010059062A |
Foreign References:
| WO1997024308A1 | ||||
| WO2014144610A1 |
Other References:
Theodora W. Greene,Protective Groups in Organic Synthesis,米国,John Willey & Sons, Inc.,1999年,第3版,P293-309
Siderhurst, Matthew S.; Jang, Eric B.; Hara, Arnold H.; Conant, PatrickEntomologia Experimentalis et ,N-butyl (E)-7,9-decadienoate: sex pheromone component of the nettle caterpillar, Darna pallivitta,Applicata,2007年,125(1),63-69
Sasaerila, Yorianta 他,Decadienoates: sex pheromone components of nettle caterpillars Darna trima and D. bradleyi,Journal of Chemical Ecology ,2000年,26(8),1969-1981
Bestmann, Hans Juergen; Suess, Joachim; Vostrowsky, Otto,Pheromones. XXXIV. Synthesis of conjugated-unsaturated Lepidoptera pheromones and analogs,Liebigs Annalen der Chemie,1981年,(12),2117-38
Krapcho, A. Paul,Synthetic applications of dealkoxycarbonylations of malonate esters, β-keto esters, α-cyano esters and related compounds in dipolar aprotic media - part I,Synthesis,1982年,(10),805-22
Suemune, Hiroshi 他,Synthesis by microbial reduction of (S)-13-hydroxy-9Z,11E-octadecadienoic acid, a defensive substance in rice,Chemical & Pharmaceutical Bulletin ,1985年,33(5),2168-70
Siderhurst, Matthew S.; Jang, Eric B.; Hara, Arnold H.; Conant, PatrickEntomologia Experimentalis et ,N-butyl (E)-7,9-decadienoate: sex pheromone component of the nettle caterpillar, Darna pallivitta,Applicata,2007年,125(1),63-69
Sasaerila, Yorianta 他,Decadienoates: sex pheromone components of nettle caterpillars Darna trima and D. bradleyi,Journal of Chemical Ecology ,2000年,26(8),1969-1981
Bestmann, Hans Juergen; Suess, Joachim; Vostrowsky, Otto,Pheromones. XXXIV. Synthesis of conjugated-unsaturated Lepidoptera pheromones and analogs,Liebigs Annalen der Chemie,1981年,(12),2117-38
Krapcho, A. Paul,Synthetic applications of dealkoxycarbonylations of malonate esters, β-keto esters, α-cyano esters and related compounds in dipolar aprotic media - part I,Synthesis,1982年,(10),805-22
Suemune, Hiroshi 他,Synthesis by microbial reduction of (S)-13-hydroxy-9Z,11E-octadecadienoic acid, a defensive substance in rice,Chemical & Pharmaceutical Bulletin ,1985年,33(5),2168-70
Attorney, Agent or Firm:
Mitsuo Matsui
Hiroshi Murakami
Yukari Kato
Hiroshi Murakami
Yukari Kato