Tetrabutylammonium Fluoride → 4-Ethynyl-benzeneacetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 10 g of 4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester in 950 ml of tetrahydrofuran is mixed at 0° C. with 45 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran. The reaction mixture is stirred for 15 minutes at 0° C. and for 2 hours at room temperature and then concentrated by evaporation. The residue is spread between water and ethyl acetate, the organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-7% ethyl acetate. 5.6 g of 4-ethinylphenylacetic acid methyl ester is obtained as oily crude product.

Provenance & Evidence