Ozone → (RS)-2-(2-oxoethyl)-6-methoxycarbonyl-1-indanone

Participants

Reaction Steps

An ozone stream (3 g ozone/hour) was conducted for 45 minutes while stirring through a solution, cooled to -70°, of 10.5 g of (RS)-2-(2-buten-1-yl)-6-methoxycarbonyl-1-indanone in 150 ml of anhydrous dichloromethane. Subsequently, the mixture was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 4.74 ml of dimethyl sulfide, the mixture was stirred at room temperature for 18 hours. The reaction mixture was evaporated in a vacuum and purified by column chromatography on silica get (diethyl ether). By recrystallization of the resulting solid, there were obtained 4.5 g (45%) of (RS)-2-(2-oxoethyl)-6-methoxycarbonyl-1-indanone as a light yellow solid with m.p. 92°.

Provenance & Evidence