Dimethylformamide → trans Methyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

HRID 1605133Notes

Reaction equation

HRID 1605133 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][S:5][C:6]([CH3:16])([CH3:15])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=O.CN(C)[CH:19]=[O:20]>>[CH3:4][S:5][C:6]([CH3:16])([CH3:15])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:14])[CH2:11]/[CH:12]=[CH:15]/[C:6]([CH3:16])=[CH:7][C:1]([O:20][CH3:19])=[O:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 215493787-Methylthio-3,7-dimethyloctan-1-al

Product 1

HCID 86733216trans Methyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

Procedure

Sodium methoxide (1.2 g. of sodium and 30 ml. of methanol) is added slowly to a mixture of 6.4 g. of 7-methylthio-3,7-dimethyloctan-1-al and 10 g. of diethyl 3-methoxycarbonyl-2-methylprop-2-enyl phosphonate (about 77% trans) in 50 ml. of dimethylformamide, under nitrogen and at about 0°, with stirring. After addition is complete, the reaction is left 3 hours at room temperature and worked up by extraction with hexane/ether to yield cis/trans methyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate mostly the trans, trans isomer.

Workup

  1. additionAfter addition
  2. extractionworked up by extraction with hexane/ether

Sources & evidence

ORD record
ord-b61af519aaa34949b0ae7d5ddc99c527
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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