Sodium hydride → HCID 22058664, compound

Participants

Reaction Steps

4,5-Dibromo-2-methylimidazole (4.91 g) was dissolved in N,N-dimethylformamide (50 ml), and 60% sodium hydride (901 mg) was added gradually under ice-cooling. After stirring at room temperature for 1 hour, 2-(trimethylsilyl)ethoxymethyl chloride (3.75 g) was gradually added dropwise under ice-cooling, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure and ethyl acetate was added to the residue. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give 4,5-dibromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole (7.6 g) as a colorless oil.

Provenance & Evidence