Tetrahydrofuran → 7-(1-Ethyl-1-hydroxypropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of ethylmagnesium bromide (3M solution in diethyl ether; 32 mL, 96 mmol) was added dropwise to a suspension of methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (5.00 g, 24.2 mmol) in tetrahydrofuran (50 mL) at 0° C. The mixture was stirred at 40° C. overnight. The reaction was quenched with water and 1N HCl, extracted with ethyl acetate, washed with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was crystallized from ethanol/diethylether to afford the title compound as colorless crystals (3.39 g, 70%). mp 199-201° C.

Provenance & Evidence