Dimethyl Sulfide → HCID 21848315, compound

Participants

Reaction Steps

Ozone was conducted at -78° C. into a solution of 6.6 g (34 mmol) of a 4:1 mixture of 4-fluoro-2-methyl-7-propyl-benzofuran and 4-fluoro-2-methyl-7-propyl-2,3-dihydro-benzofuran until the color became blue. Subsequently, argon was conducted through the solution which was then treated at -78° C. with 13 ml of dimethyl sulfide. After warming to room temperature the solution was concentrated in a vacuum and the residue was dissolved in 50 ml of ethanol. After the addition of 50 ml of 3% sodium hydrogen carbonate solution the mixture was stirred at 70° C. for 30 minutes. Subsequently, the mixture was poured on to 200 ml of ice-water, made acid with 10% HCl and extracted three times with 150 ml of diethyl ether each time. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane/hexane 2:3). There were obtained 5.0 g (100%) of 6-fluoro-2-hydroxy-3-propyl-benzaldehyde as a pale yellow oil, which was used immediately in the next reaction.

Provenance & Evidence