Triphenylphosphine → HCID 66817873, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(2-oxo-ethyl)-cyclohexanecarboxylic acid benzyl ester (trans:cis=4:1) (21.4 mg, 0.082 mmol) in dimethylformamide (0.3 ml) was added to a solution of sodium chlorodifluoroacetate (34.1 mg, 0.224 mmol) and triphenylphosphine (59.9 mg, 0.228 mmol) in dimethylformamide (0.41 ml) at 90 to 95° C. over five minutes, and the mixture was stirred at 130° C. for four hours. Sodium chlorodifluoroacetate (34.0 mg, 0.22 mmol) was then added to the reaction mixture at the same temperature, and the mixture was further stirred for two hours. The reaction mixture was diluted with ether, and the organic layer was washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-(3,3-difluoro-allyl)-cyclohexanecarboxylic acid benzyl ester (trans:cis=4:1) (14.1 m, 58%).

Provenance & Evidence