Dimethyl Sulfoxide → HCID 86758779, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (0.30 mL, 3.5 mmol) in anhydrous dichloromethane (30 mL) at −78° C. under nitrogen atmosphere, dimethylsulfoxide (0.51 mL, 7.2 mmol) was added and stirred for 30 minutes. To this mixture, a solution of ethyl (1SR,2SR,3RS)-2-hydroxymethyl-3-vinylcyclopropane carboxylate (490 mg, 2.9 mmol) in anhydrous dichloromethane (20 mL) was added and reaction stirred at the same temperature for 45 minutes. Then, triethylamine (2.0 mL, 14.4 mmol) was added and mixture was allowed to react at room temperature. After 30 minutes, the reaction was quenched with water (30 mL), the layers were separated and the aqueous one was extracted with dichloromethane (2×30 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The resulting residue was purified by column chromatography using ethyl acetate and hexane 1:4 as eluent to afford 460 mg (95% yield) of ethyl (1SR,2SR,3RS)-2-formyl-3-vinylcyclopropane carboxylate.

Provenance & Evidence