Aluminium lithium hydride → 1-Trityl-1H-benzimidazol-5-yl-methanol

Participants

Reaction Steps

To an ice-cooled stirred suspension of the product of step b (3.61 g, 7.94 mmol) in THF (30 ml) was added dropwise a solution of lithium aluminium hydride (1.0M in THF, 10 ml, 10.0 mmol). The suspension was stirred at this temperature for 1 h and then was quenched with saturated aqueous ammonium chloride (100 ml). The aqueous solution was extracted thrice with ethyl acetate (100 ml) and the combined organic phases were washed with brine (200 ml). The organic phase was dried over magnesium sulfate and the filtrate was evaporated at reduced pressure and the residue recrystallised from ethyl acetate/hexane to afford the title compound (2.68 g, 79%). 1H NMR 7.89 (1H, s), 7.74 (1H, d, 8.4), 7.33-7.17 (17H, m), 6.44 (1H, d, 0.9), 4.45 (2H, d, 6), 1.37 (1H, t, 6).

Provenance & Evidence