Triphenylphosphine → HCID 86747637, compound

Participants

Reaction Steps

To a stirred solution of trans-4-cyano-5-hydroxymethyltetrahydrothiophene (78 mg) and triphenylphosphine (283 mg) in THF (3 ml), diethylazodicarboxylate (188 mg) dissolved in THF (1.2 ml) and thioacetic acid (82 mg) dissolved in THF (1.2 ml) were added dropwise under ice-cooling and the mixture was stirred for 30 minutes. Saturated aqueous sodium bicarbonate solution was added to the mixture and extracted with diethylether. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 94 mg (86%) of trans-5-acetylthiomethyl-4-cyanotetrahydrothiophene.

Provenance & Evidence