Chlorotrimethylsilane → 4-(3-Formyl-n-propyl)-1-trimethylsilylimidazole

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Reaction Steps

A solution of 1.82 g of 4-(3-ethoxycarbonylpropyl)-1H-imidazole in 30 ml of tetrahydrofuran under nitrogen is treated with 0.5 g of sodium hydride (50% oil dispersion) at 0° for 30 minutes and 1.45 ml of trimethylsilyl chloride at 0° for 3 hours. The reaction mixture is washed with cold 0.5N sodium bicarbonate solution, dried over sodium sulfate and evaporated to dryness. The oil is redissolved in 100 ml of methylene chloride at -78° under nitrogen and 12.82 ml of diisobutyl-aluminum hydride (1.56M) is added dropwise. The reaction mixture is stirred for 5 minutes at -78°, quenched with 1 ml of methanol followed by 10 ml of water and filtered through Celite®. The organic phase is separated, dried over sodium sulfate and evaporated to yield the title compound (a).

Provenance & Evidence