6-Methyl-5-hepten-2-one → 3,7-Nonadienoic acid, 4,8-dimethyl-, methyl ester

HRID 2164186노트

반응식

HRID 2164186 반응식
[CH3:1]C(C)=CCCC(=O)C.[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([OH:16])=[O:15].[Cl-].[C:24]([CH2:27]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O>CS(C)=O>[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([O:16][CH3:1])=[O:15].[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([O:16][CH2:24][CH3:27])=[O:15]

참가 물질

6

반응물 3

HCID 98626-Methyl-5-hepten-2-oneHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 54343890HCID 54343890, 화합물

생성물 2

HCID 5497503,7-Nonadienoic acid, 4,8-dimethyl-, methyl esterHCID 53706627Ethyl 4,8-dimethylnona-3,7-dienoate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

6-Methyl-5-hepten-2-one is converted into 4,8-dimethylnona-3,7-dienoic acid by reaction with β-carboxyethyltriphenylphosphonium chloride in dimethylsulfoxide using the method of H. S. Corey et al., J. Am. Chem. Soc. 86, 1884 (1964). The trans and cis isomer can be separated by chromatography at this point or a mixture of the two isomers employed in further reactions. The acid is then converted into the acid chloride using thionyl chloride at roomm temperature or slightly higher. The acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes to yield the ester, methyl 4,8-dimethylnona-3,7-dienoate and ethyl 4,8-dimethylnona-3,7-dienoate.

후처리

  1. customThe trans and cis isomer can be separated by chromatography at this point
  2. additiona mixture of the two isomers
  3. additionThe acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes

출처 및 근거

ORD 기록
ord-f0581ef25f564578bbff1248f7c1f3af
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04137273

반응 노트

불러오는 중…