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

HRID 1605143Notes

Reaction equation

HRID 1605143 reaction equation
[O-][CH2:2]C.[Na+].[CH2:5]([O:7][C:8]([CH:10]=[C:11]([CH3:21])[CH2:12]P(=O)(OCC)OCC)=[O:9])[CH3:6].[CH3:22][S:23][C:24]([CH3:34])([CH3:33])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:32])[CH2:29]C=O.CN(C)C=O>O>[CH3:22][S:23][C:24]([CH3:33])([CH2:25][CH2:26][CH2:27][CH:28]([CH3:29])[CH3:32])[CH2:34][CH:2]=[CH:12][C:11]([CH3:21])=[CH:10][C:8]([O:7][CH2:5][CH3:6])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2723922Sodium ethoxideHCID 2773818Ethyl 4-(diethoxyphosphoryl)-3-methylcrotonateHCID 215493787-Methylthio-3,7-dimethyloctan-1-al

Product 1

HCID 54030089Ethyl 7-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium ethoxide (490 mg.) is added, during about 10 minutes and under nitrogen, to a stirred solution of diethyl 3-ethoxycarbonyl-2-methylprop-2-enylphosphonate (1.93 g.) and 7-methylthio-3,7-dimethyloctan-1-al (1.35 g.) in 20 ml. of dimethylformamide, cooled to 0°. The reaction mixture is stirred at room temperature for about 16 hours and then is diluted with water and extracted with ether. The ethereal extracts are washed with brine, dried over calcium sulfate and evaporated to yield ethyl 7-methylthio-3,7,11-trimethyldodeca-2,4-dienoate, predominantly the trans, trans isomer, which can be purified by chromatography or distillation.

Workup

  1. extractionextracted with ether
  2. washThe ethereal extracts are washed with brine
  3. dry with materialdried over calcium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-27ec5519239540e290da6461f26c43f7
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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