Dimethyl Sulfide → HCID 21848322, compound

Participants

Reaction Steps

Ozone was conducted at -78° into a solution of 4.8 g (25 mmol) of 6-fluoro-2-methyl-7-propyl-benzofuran until the colour became blue. Subsequently, argon was conducted through the solution which was then treated at -78° with 10 ml (136 mmol) of dimethyl sulfide. After warming to room temperature the solution was concentrated in a vacuum and the residue was dissolved in 40 ml of ethanol. After the addition of 20 ml of 3% sodium hydrogen carbonate solution the mixture was stirred at 70° 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). There were obtained 3.3 g (72%) of 4-fluoro-2-hydroxy-3-propyl-benzaldehyde as a pale yellow oil.

Provenance & Evidence