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

HRID 1605138ノート

反応式

HRID 1605138 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0afdc93b3e2142dc8b0c7ebc8e27e4cc
出典データセット
uspto-grants-1976_04
特許番号
US03948996

反応ノート

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