Sodium Thiosulfate → HCID 178527306, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask containing trans-4-[4-(phenylsulfanyl)cyclohexyl]-1,3-benzenediol (18 mg, 0.06 mmol) and dichloromethane (2 ml) was cooled to 0° C. and meta-chloroperbenzoic acid (50-60%, 41 mg, 0.24 mmol) was added with stirring. After 30 min at this temperature the reaction mixture was poured into saturated sodium thiosulfate solution (5 ml) and partitioned between saturated aqueous sodium hydrogen carbonate (10 ml) and dichloromethane (10 ml). The aqueous phase was further extracted with dichloromethane (2×10 ml) and the combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification via flash column chromatography (SiO2, ethyl acetate/petrol, 30:70) afforded the title compound (6 mg, 30%) as an off-white solid. δH (d4-MeOH) 1.40-1.62 (4H, m), 1.88-1.95 (2H, m), 2.05-2.13 (2H, m), 2.72 (1H, m), 3.18 (1H, m), 6.08-6.13 (2H, m), 6.82 (1H, d), 7.64 (2H, m), 7.75 (1H, m), 7.90 (2H, m); m/z (ES+) 333 (M+H)+.

Provenance & Evidence