Acetate → HCID 22414832, compound

Participants

Reaction Conditions

Reaction Steps

Ozone was bubbled through a solution of 8.2 g (22.6 mmol) of 4-acetoxy-5-allyl-1-benzyl-2,3-dihydro-3,3,7-trimethyl-1H-indol-2-one in 2 l of ethyl acetate for 3 hours under cooling with ice. After bubbling nitrogen through the reaction mixture, 34.6 g (558 mmol) of dimethylsulfide was added and the mixture was stirred for one hour at 50° C. The solvent was evaporated and the residue was dissolved in 800 ml of methanol, followed by addition of 15.7 g (47 mmol) of methyltriphenylphosphoranilidene acetate. The mixture was stirred overnight. After evaporating the solvent from the reaction mixture, the residue was purified by column chromatography (silica gel, 3:1 mixture of n-hexane and ethyl acetate) to obtain 1.5 g (yield, 15.7%) of the title compound (a) and 480 mg (yield, 5.0%) of the title compound (b), each as a light yellow oil.

Provenance & Evidence