m-Chloroperbenzoic acid → Dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioate

Participants

Reaction Steps

To a cooled solution (−78° C.) of dibenzyl 2-[(benzylsulfonyl)methyl]pentanedioate (8.2 g, 18.3 mmol) in dichloromethane (100 mL), was added 3-chloroperbenzoic acid (85%, 8.2 g, 40.3 mmol) with stirring. The reaction mixture was allowed to warm to room temperature. White solids precipitated from the reaction mixture. After 2 hours at room temperature, the reaction mixture was filtered and the white solids washed with dichloromethane. The filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate and the dichloromethane removed under reduced pressure. The resulting oil was purified by column chromatography to yield 7.5 g (85%) of clear oil.

Provenance & Evidence