Sodium sulfate decahydrate → 1-Benzyl-5-benzimidazolemethanol

Participants

Reaction Steps

0.87 g of methyl 1-benzyl-5-benzimidazolecarboxylate (prepared as described in Preparation 27) in 18 ml of dehydrated tetrahydrofuran were added to a suspension of 0.23 g of lithium aluminum hydride in 10 ml of dehydrated tetrahydrofuram, whilst ice-cooling, and the resulting mixture was stirred for 2 hours at room temperature. A further 0.11 g of lithium aluminum hydride and 10 ml of dehydrated tetrahydrofuran were then added to the reaction mixture and the mixture was stirred for 1 hour at room temperature and then for 4.5 hours at 50° C. in oil bath, after which it was heated under reflux for 2 hours. The reaction mixture was cooled to room temperature by allowing it to stand, after which sodium sulfate decahydrate was added to it in excess and the mixture was stirred for 2 hours at room temperature. At the end of this time, the reaction mixture was filtered with the aid of a Celite (trade mark) filter aid and the filtrate was freed from the solvent by distillation under reduced pressure. The residue was then recrystallized from a mixture of ethanol and diisopropyl ether, to give 383 mg of the title compound, melting at 148°-150° C.

Provenance & Evidence