Tetrahydrofuran → 4-(Methanesulfinyl)-4-(methylsulfanyl)cyclopent-1-ene

Participants

Reaction Conditions

Reaction Steps

Potassium hydride (4.2g) was suspended in 50 ml. of tetrahydrofuran, and 5.464 g of formaldehyde dimethyl mercaptal S-oxide was added dropwise at -10° C. to 0° C. The mixture was stirred for 1 hour at 0° C., and then a tetrahydrofuran solution (6.585 g/30 ml.) of cis-1,4-dichloro-2-butene was added while adjusting the temperature of the reaction mixture to -30° to -40° C. Then, the mixture was stirred for 12.5 hours at room temperature. Methylene chloride (400 ml) and 50 ml. of water were added, and the mixture was shaken. The organic phase was separated, and the aqueous phase was extracted with methylene chloride. The extract and the organic phase were combined, dried with anhydrous sodium sulfate, and concentrated at reduced pressure. The residue was separated by column chromatography (Florisil, eluted with methylene chloride) to afford 3.461g of 3-cyclopentenone dimethyl mercaptal S-oxide in a yield of 45%.

Provenance & Evidence