Water → HCID 68670895, compound

Participants

Reaction Steps

Ethyl 2-[3-bromo-4-(cyclopropylsulfanyl)phenyl]-3-[(2S,3S,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]acrylate (2.58 g, (E)/(Z)-mixture) was dissolved in dichloromethane (77 mL), followed by ice-cooling. To this solution was added sodium hydrogen carbonate (7.87 g) and then m-chloroperbenzoic acid (2.31 g). It was stirred for 30 minutes under ice-cooling, and further warmed to room temperature, followed by stirring for 3 hours. Dichloromethane (55 mL) and m-chloroperbenzoic acid (0.32 g) were further added thereto, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture to stop the reaction and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-[(2S,3S,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]acrylate (2.52 g) as an (E)/(Z)-mixture of olefin.

Provenance & Evidence