Methanol → HCID 19094244, compound

Participants

Reaction Steps

A suspension of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazole-7-carboxylic acid (Example 3) (9.06 g, 26.4 mmol) in dry tetrahydrofuran (950 mL) under an argon atmosphere was treated dropwise with a solution of diborane in tetrahydrofuran (105.2 mL of 1M diborane). The mixture was stirred at ambient temperature overnight. The reaction was cooled, treated with excess methanol continuously and the solvents were evaporated. The residue was dissolved in methylene chloride, and the solution was washed well with water, dried and concentrated. The crude product was chromatographed over 500 g of silica gel with a gradient of methanol in methylene chloride to give about 5 g of product. This was boiled in 10% hydrochloric acid (100 mL) and then chilled. The yellow crystals were filtered to provide 4.78 g of 2-n-butyl-1-(2-chlorophenyl)methyl-7-hydroxymethyl-1H-benzimidazole hydrochloride; mp 223°-233.5° C.

Provenance & Evidence