Triethylamine → ((e)-4,4,4-Trifluoro-but-2-ene-2-sulfonyl)-benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 14.0 mmol rac-(4,4,4-trifluoro-2-iodo-butane-2-sulfonyl)-benzene in 25 ml tetrahydrofuran and 2.5 ml water were added 42.1 mmol triethylamine and 42.1 mmol potassium carbonate. The mixture was heated at 70° C. for 6 h. The reaction mixture was then diluted with ethyl acetate and was washed sequentially with 1 N hydrochloric acid and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a yellow oil (yield 72%). EI-MS (m/e): 250.1 (M+, 15%), 186.1 ([M−SO2]+, 38%), 125.0 (PhSO+, 100%), 77.1 (Ph+, 38%).

Provenance & Evidence