Ethyl 4-(diethoxyphosphoryl)-3-methylcrotonate → Isopropyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

HRID 1605138노트

반응식

HRID 1605138 반응식
[CH3:1][S:2][C:3]([CH3:13])([CH3:12])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:11])[CH2:8][CH:9]=O.[CH2:14]([O:16][C:17]([CH:19]=[C:20]([CH3:30])[CH2:21]P(=O)(OCC)OCC)=[O:18])[CH3:15].[CH:31]([O-])(C)C.[Na+]>CN(C)C=O>[CH3:1][S:2][C:3]([CH3:13])([CH3:12])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:11])[CH2:8][CH:9]=[CH:21][C:20]([CH3:30])=[CH:19][C:17]([O:16][CH:14]([CH3:15])[CH3:31])=[O:18]

참가 물질

5

반응물 3

HCID 2773818Ethyl 4-(diethoxyphosphoryl)-3-methylcrotonateHCID 109204432-Propanol, sodium salt (1:1)HCID 215493787-Methylthio-3,7-dimethyloctan-1-al

생성물 1

HCID 54300429Isopropyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 10 g. of 7-methylthio-3,7-dimethyloctan-1-al, 17 g. of diethyl 3-ethoxycarbonyl-2-methylprop-2-enyl-phosphonate (77% trans), and 150 ml. of dimethylformamide, under nitrogen, 0°, with stirring, is added sodium isopropanolate (prepared from 1.5 g. of sodium in 150 ml. of isopropanol). After addition is complete, the reaction is stirred for 18 hours at room temperature and then worked up by extraction with hexane to yield isopropyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate (mostly trans-2,trans-4) which can be chromatographed and distilled for further purification.

후처리

  1. additionTo a mixture of 10 g
  2. additionAfter addition
  3. extractionworked up by extraction with hexane

출처 및 근거

ORD 기록
ord-0afdc93b3e2142dc8b0c7ebc8e27e4cc
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03948996

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