Dimethyl Sulfoxide → HCID 58368470, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulfoxide (0.064 mL, 0.90 mmol) was added to oxalyl chloride (0.048 mL, 0.56 mmol) in methylene chloride (2.1 mL) at −78° C. After 10 minutes, [4-chloro-7-(3-fluorophenyl)-2,1-benzisoxazol-6-yl]methanol (0.104 g, 0.374 mmol) in methylene chloride (4.2 mL) was added and the resulting mixture was stirred at −78° C. for 30 minutes. Triethylamine (0.261 mL, 1.87 mmol) was then added and the mixture was stirred for 5 hours at room temperature. After quenching with water, the mixture was extracted with methylene chloride. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated to dryness. The resulting mixture was purified on silica gel, eluting with 0 to 30% ethyl acetate in hexane, to give the desired product (88 mg, 85%). LCMS calculated for C14H8ClFNO2 (M+H)+: m/z=276.0; Found: 276.1.

Provenance & Evidence