m-Chloroperbenzoic acid → HCID 178472329, compound

Participants

Reaction Steps

A solution of ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (308 mg, 0.895 mmol) from Step 1 in dichloromethane (10 mL) was treated portionwise at 0° C. with meta-chloroperbenzoic acid (261 mg, 1.163 mmol, 77%). The mixture was stirred at room temperature for 16 h, diluted with dichloromethane and washed with 2N sodium hydroxide. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with brine, dried over magnesium sulfate and filtered. The volatiles were removed under reduced pressure and the crude product was purified by chromatography on silica gel (0% to 20% EtOAc in hexanes) to afford ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]cyclohexanecarboxylate as a colorless oil. MS ESI calc'd. for C14H18BrNO3S [M+H]+ 360, 362. found 360, 362.

Provenance & Evidence