Thiirane → HCID 21411767, compound

Participants

Reaction Steps

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by sodium metal (6.3 gms) in small pieces. The mixture was allowed to stand for 30 minutes and 3-(4-pyridyl)-propan-1ol (19 gms) was then added. A deep yellow colour was allowed to develop over a period of 2 hours after which time ethylene sulphide (8.3 gms) was added quickly. A vigorous reaction occurred and the mixture was stirred for a further 4 hours. Ammonium chloride (10 gms) was added and the solvent was allowed to evaporate overnight. The residual tacky solid was extracted into pyridine and the mixture was filtered and the solvent evaporated. Distillation of the residual oil yielded 3-(4-pyridyl)-5-hydroxy-pentane-1-thiol (12.7 gms, 60% conversion); b.p. 177°-185° C/1 mm Hg, m.p. 50°-52° C, characterised by the following spectra:

Provenance & Evidence