m-Chloroperbenzoic acid → 4-[4-(methylsulfinyl)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Participants

Reaction Steps

A solution of meta-chloroperbenzoic acid (5.08 g, 22.66 mmol) in dichloromethane (30 ml) was added dropwise over 15 minutes at 0° C. to a solution of 4-[4-(methylthio)phenyl]tetrahydro-2H-pyran-4-carbonitrile (4.8 g, 20.6 mmol) in dichloromethane (40 ml). The reaction mixture was warmed to room temperature over 4 hours. The mixture was then diluted with dichloromethane (180 ml), washed with sodium sulphite solution and 10% aqueous sodium carbonate. The organic layer was separated, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 95:5:0.5 by volume) to provide the title compound (4.55 g, 89%) as an off-white solid. LRMS APCI+ m/z 250 [MH]+.

Provenance & Evidence