3-Furaldehyde → 2-(3-Furyl)-1-(methylsulfinyl)-1-(methylthio)ethylene

Participants

Reaction Conditions

Reaction Steps

To 20 ml of methyl methylsulfinylmethyl sulfide, 1.34 g (33.5 mmol) of powdered sodium hydroxide was added, followed by stirring at 80° C. for 30 minutes. This mixture was added to 9.627 g (100.2 mmol) of 3-furaldehyde, followed by stirring at 80° C. for 3 hours. After this was cooled to room temperature, water was added, followed by 3 extractions with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/2) to yield 2-(3-furyl)-1-(methylsulfinyl)-1-(methylthio)ethylene.

Provenance & Evidence