Methanol → HCID 178504695, compound

Participants

Reaction Steps

To a solution of 85 mg of 1-[1-(1-ethoxyethyl)-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-1H-imidazol-2-yl]-2,2,2-trifluoroethanone (Example 89, Step 1) (0.18 mmol) in 1 ml of methanol at 0° C. was added 10 mg of sodium borohydride (0.26 mmol). The solution turned immediately from yellow to colorless. The reaction was quenched with 1% solution of aqueous hydrochloric acid and diluted with methylene chloride then washed with brine. The organic extracts were dried (MgSO4), filtered and the solvent was removed under reduced pressure to provide 77.1 mg of a white film. All of this material was dissolved in 8 ml of methanol/THF (1.6:1). Oxone® (450 mg) was dissolved in 2 ml of water and the solution was added all at once. After stirring the reaction at 25° C. for 1.5 hours, the reaction was poured into water and extracted with methylene chloride. The organic extracts were dried (MgSO4) and evaporated under reduced pressure to give a white foam which was purified by preparative thin layer chromatography (SiO2; 100% ethyl acetate) to give 50.5 mg of the desired sulfone: mp 126-130° C. Anal. Calc'd. for C18H14F4N2O3S: C, 51.49; H, 3.54; N 6.33. Found: C, 51.53; H, 3.26; N, 6.31.

Provenance & Evidence