Water → HCID 22621288, compound

Participants

Reaction Steps

s-Butyllithium (0.24 ml of a 1.3M solution in hexanes) was added dropwise to a solution of 4-phenylsulphonyl-2-fluorophenylethyne (Method 28) (0.08 g) in dry THF (3 ml) at −50° C. After 25 minutes a solution of 1,1,1-trifluoroacetone (0.035 g) in dry THF (0.5 ml) was added and the mixture was allowed to warm to ambient temperature overnight. Water (10 ml) was added and THF was evaporated off under reduced pressure. The residue was diluted with water (30 ml) and extracted with ethyl acetate (30 ml). The organic layer was washed with brine then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-30% ethyl acetate/hexane then triturated with hexane to give the title compound (0.038 g) as a solid. NMR (CDCl3): 1.75 (s, 3H), 2.75 (s, 1H), 7.5-7.75 (m, 6H), 7.93 (d, 2H); EA: C17H12F4O3S requires C, 54.8; H, 3.3%; found: C, 54.4; H, 3.4%.

Provenance & Evidence