Butyl-p-toluenesulfonate → Hydrochloric Acid

Participants

Reaction Steps

To a solution of (R)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-mercapto-2-propanol (II) (3 g) in dry N,N-dimethylformamide (20 ml) were added a 50% dispersion of sodium hydride in paraffin (1 g) and n-butyl p-toluenesulfonate (2.3 g) at 0°-5° C. in nitrogen atmosphere. The mixture was stirred at 0°-5° C. for 1 hour and at 20°-25° C. for 18 hours. The reaction mixture was diluted with water (200 ml) and extracted with dichloromethane. Treatment of the extract in the same manner as in Example 4 gave (R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (I: n=3) hydrochloride (2.5 g). Yield, 63.8%. M.P., 168°-169° C. [α]D20 -88.8° (c=1, methanol).

Provenance & Evidence