Pyridine → beta,beta,beta-Trichloroethoxycarbonylsulfenyl Chloride

Participants

Reaction Steps

To an ice cold vigorously stirred (mechanical stirrer) solution of trichloroethanol (50.0 ml, 0.52 mol) and pyridine (42.0 ml, 0.52 mol) in 300 ml of methlene chloride, chlorocarbonylsulfenyl chloride (43.5 ml, 0.52 mol) was added dropwise over 30 min. After the addition the solution was stirred at 0° for 1.5 hr. The ice bath was removed and the stirring continued for 1.5 hr. The mixture (solid formed) was washed with ice--H2O and ice cold sat. NaCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure. After removal of the solvent an oily solid remained. The solid was removed by triterration with ether and filtration of the solid. The filtrate was condensed under reduced pressure and the process repeated until, after removal of the solvent from the filtrate, the liquid could be filtered without the aid of solvent. The yellow liquid was distilled under reduced pressure: bp 54°-59° (0.25 mm; bath temp. 80°-90°); NMR (CDCl3 ) δ 5.0 (S, 2H).

Provenance & Evidence