Ozone → HCID 10560109, compound

Participants

Reaction Steps

Ozone (3 g ozone/hour) was conducted while stirring for 85 minutes through a solution, cooled to -70°, of 19.2 g of (RS)-2-(2-buten-1-yl)-5-methoxy-1-indanone in 600 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen and then 9.1 ml of dimethyl sulfide were added to the cold solution. The solution came to room temperature overnight and was evaporated in a vacuum. The residue was chromatographed (dichloromethane) over a column with oxalic acid solution adsorbed on silica gel (600 g silica gel; 100 ml 10% oxalic acid solution). 14.1 g (78%) of (RS)-2-(2-oxoethyl)-5-methoxy-1-indanone were obtained as a yellow oil.

Provenance & Evidence