Ethyl Acetate → HCID 19801010, compound

Participants

Reaction Steps

In dichloromethane (15 ml) was dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (1.50 g). To the solution was added dropwise, under ice-cooling, chloroacetyl isocyanate (0.46 ml). The mixture was stirred for 20 minutes, which was diluted with ethyl acetate (60 ml) and 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, and the residue was purified by means of a silica gel column chromatography (carrier 75 g, developing solvent : ethyl acetate - hexane=1:2), followed by crystallization from ether-hexane to afford 4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (1.70 g: yield 83%) as colorless crystals, m.p. 101° to 102° C.

Provenance & Evidence