Dimethyl Sulfide → HCID 15341581, compound

Participants

Reaction Conditions

Reaction Steps

Ozone is sparged for 3 h 30 min into a solution of 12.5 g (0.039 mol) of trans-7-benzyloxy-3-ethenyl-3,3a,4,5-tetrahydro-1H-oxazolo[3,4-a]quinolin-1-one in 450 ml of dichloromethane and 350 ml of methanol, cooled to -40° C. The excess ozone is then stripped off with a stream of nitrogen, 14.8 g (0.39 mol) of sodium borohydride are added in small portions, followed by 12.6 g (0.195 mol) of dimethyl sulphide, and the mixture is left overnight at room temperature. It is extracted twice with dichloromethane, the organic phase is washed with water and then with saturated sodium chloride solution and dried, and the solvent is evaporated off under reduced pressure. After purification by chromatography on a column of silica, with a 95/5 mixture of dichloromethane and methanol, 10.9 g of product are obtained.

Provenance & Evidence