Dimethyl Sulfoxide → HCID 22718712, compound

Participants

Reaction Steps

A suspension of 60% sodium hydride (1.2 g,30 mmol) in tetrahydrofuran (30 mL)-dimethyl sulfoxide (30 mL) was heated at external temperature of 60° C., and trimethylsulfoxonium iodide (6.5 g, 30 mmol) was added portionwise to the mixture. The resultant mixture was stirred for 1 hour and then cooled to room temperature. A solution of 1-(2-(benzyloxy)-5-chlorophenyl)-1-ethanone [compound (9-1)] (5.0 g, 19 mmol) in tetrahydrofuran (10 mL) was added dropwise to the mixture, and the mixture was stirred for 3 hours at external temperature of 60° C. After the mixture was cooled to room temperature, the mixture was added to ice-water, followed by extraction with diethyl ether. The extracted substance was washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure, to thereby yield 2-(2-(benzyloxy)-5-chlorophenyl)-2-methyloxirane as a colorless oily product (yield: 4.4 g). The obtained product was used in the subsequent reaction step without purification.

Provenance & Evidence