Chlorotrimethylsilane → Hexa-2,4-dienoic acid methyl ester

HRID 2245754Notes

Reaction equation

HRID 2245754 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].[CH3:9][Si](Cl)(C)C>CO.C(Cl)Cl>[CH3:9][O:7][C:1](=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6]

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 643460Sorbic Acid

Product 1

HCID 61197Hexa-2,4-dienoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of sorbic acid (1.12 g, 10 mmol) in dry methanol (50 mL) was added dropwise a solution of trimethylsilyl chloride (2M, 12 mL) in CH2Cl2. After stirring for 16 hours, the mixture was concentrated under reduced pressure to give a pale yellow oil that was purified by flash chromatography (9:1 60-80° C. petroleum ether:diethyl ether) to give the title compound (1.23 g, 99%) as a colourless oil.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a pale yellow oil that
  3. customwas purified by flash chromatography (9:1 60-80° C. petroleum ether:diethyl ether)

Sources & evidence

ORD record
ord-cb264acdd6244927bb34afc881d9c32d
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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