Ethyl Acetate → HCID 86746495, compound

Participants

Reaction Steps

4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylsulfinylmethyl-1,4-cyclohexanediol (300 mg) was dissolved in dichloromethane (2 ml), to which was added, under ice-cooling, m-chloroperbenzoic acid (179 mg), and the mixture was stirred for one hour. The reaction mixture was diluted with ethyl acetate (70 ml), which was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by a silica gel column chromatography (carrier 15 g, developing solvent: ethyl acetate - hexane 2:1) to afford 4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-h-exenyl)-3-methoxy-1-phenylsulfonylmethyl-1,4-cyclohexanediol (91 mg: yield 30%) as colorless powder.

Provenance & Evidence