Sodium ethoxide → Ethyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

HRID 1605137Notes

Reaction equation

HRID 1605137 reaction equation
[O-]CC.[Na+].[CH3:5][S:6][C:7]([CH3:17])([CH3:16])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:15])[CH2:12][CH:13]=O.[CH2:18]([O:20][C:21]([CH:23]=[C:24]([CH3:34])[CH2:25]P(=O)(OCC)OCC)=[O:22])[CH3:19]>CN(C)C=O>[CH3:5][S:6][C:7]([CH3:17])([CH3:16])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:15])[CH2:12][CH:13]=[CH:25][C:24]([CH3:34])=[CH:23][C:21]([O:20][CH2:18][CH3:19])=[O:22]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 2773818Ethyl 4-(diethoxyphosphoryl)-3-methylcrotonateHCID 215493787-Methylthio-3,7-dimethyloctan-1-al

Product 1

HCID 53843923Ethyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium ethoxide (prepared from 0.2 g. of sodium and 12 ml. of ethanol) is slowly added to a mixture of 1.1 g. of 7-methylthio-3,7-dimethyloctan-1-al, diethyl 3-ethoxycarbonyl-2-methyl-prop-2-enyl-phosphonate (1.6 g.) and 50 ml. of dimethylformamide, with stirring, under nitrogen, at 0°. The reaction is stirred for 1.5 hours after addition is complete and then worked up by extraction with ether to yield ethyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate.

Workup

  1. additionafter addition
  2. extractionworked up by extraction with ether

Sources & evidence

ORD record
ord-34e331dc180e4a3596bdbd2bda225519
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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