Sodium Hydroxide → 1,4-Dimethyl-5-hydroxymethyl-2-(4-methoxybenzylthio)imidazole

Participants

Reaction Conditions

Reaction Steps

5-Carbethoxy-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (31 g, 0.1 mole) dissolved in ether (250 ml) was added dropwise to a solution of aluminum hydride in ether stirred at 0° C. [the aluminum hydride in ether was prepared by adding lithium aluminum hydride (7.4 g, 0.19 mole) in portions to a solution of aluminum chloride (8.6 g, 0.065 mole) stirred in ether (200 ml) at 0° C⟧ The mixture was stirred at 0° C. for 1 hour, treated with water and 10% aqueous sodium hydroxide, filtered and concentrated in vacuo. The resulting oil was dissolved in methylene chloride, dried with magnesium sulfate, filtered and concentrated in vacuo to give 1,4-dimethyl-5-hydroxymethyl-2-(4-methoxybenzylthio)imidazole.

Provenance & Evidence