Triphenylphosphine → Methyl 4-trimethylsilylethynylbenzoate

Participants

Reaction Conditions

Reaction Steps

21.5 g (0.1 mol) of methyl 4-bromobenzoate, 300 ml of triethylamine and a mixture of 200 mg of palladium acetate and 400 mg of triphenylphosphine were introduced into a three-necked flask under a stream of nitrogen. 20 g (0.204 mmol) of trimethylsilylacetylene were then added and the mixture was heated gradually to 90° C. over 1 hour and maintained at this temperature for 5 hours. The reaction medium was cooled, the salt was filtered off and the filtrate was evaporated. The residue was taken up in 200 ml of hydrochloric acid (5%) and 400 ml of ethyl ether. The ether phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with dichloromethane. After evaporation of the solvents, 23 g (100%) of the compound were recovered in the form of a colorless oil.

Provenance & Evidence