Hydrochloric Acid → α-Phenyl-1H-imidazole-5-methanol

Participants

Reaction Steps

A gentle stream of HCl gas was bubbled through a refluxing solution of 2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-phenyl-methyl)-imidazole-1-sulfonic acid dimethylamide (0.2 g, 0.51 mmol) in methanol (5 ml) for 1 hour. The solvent was evaporated and sodium hydroxide solution was added. The mixture was extracted with dichloromethane (2 times). The combined organic layers are dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1) to yield 25 mg (26%) of rac-5-(hydroxy-phenyl-methyl)-1H-imidazole, MS (EI): 174.1 ((M+.) and 5 mg (5%) of rac-5-(methoxy-phenyl-methyl)-1H-imidazole as colourless oil: MS (ISP): 189.1 ((M+H)+.).

Provenance & Evidence