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

HRID 1605138Notes

Reaction equation

HRID 1605138 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-0afdc93b3e2142dc8b0c7ebc8e27e4cc
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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