Methyl trifluoromethyl ketone → HCID 22419841, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-phenylsulfonylbenzothiazole (0.845 g) in dry tetrahydrofuran (50 mL) at -78° C. was added lithium diisopropylamide (3.5 mmol in 3 mL tetrahydrofuran) dropwise over approximately 10 minutes. A deep red solution formed. Trifluoroacetone (0.63 g) was added. After stirring for 20 minutes at -78° C., the reaction mixture was quenched with saturated ammonium chloride solution. The reaction mixture was then extracted with ether (75 mL and 25 mL) and dichloromethane (25 mL). The combined organic layers were dried, filtered and purified by chromatography, eluting with ethyl acetate:hexane (gradient of 10 to 30% ethyl acetate), to give the title compound as a white solid (0.558 g); m.p. 126.5°-128.5° C.; NMR: 8.62 (d,1), 8.43 (d,1), 8.01-8.07 (m,4), 7.60-7.70 (m,3), 1.84 (s,3); MS: m/z=388(M+1). Analysis for C16H 12 F3NO3S2 : Calculated: C,49.61; H,3.12; N, 3.62: Found: C, 49.43; H, 3.23; N, 3.56.

Provenance & Evidence