Sodium hydride → 1-(2-Trimethylsilanylethoxymethyl)-1H -imidazole-4-carbaldehyde

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Reaction Steps

Imidazole-4-carboxaldehyde (1 g, 10.4 mmol) was added portionwise to a solution of sodium hydride (463 mg, 60% dispersion in mineral oil, 11.4 mmol) in N,N-dimethylformamide (15 ml), and the solution stirred for 30 minutes at room temperature. 2-(Trimethylsilyl)ethoxymethyl chloride (2.03 ml, 11.4 mmol) was added and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of aqueous ammonium chloride solution, and the mixture extracted with ethyl acetate (2×). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with methanol:ethyl acetate (3:97), to give the title compound, 1.8 g, 77% yield.

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