Sodium hydride → HCID 22058664, compound

Participants

Reaction Steps

A 901 mg portion of 60% sodium hydride was added little by little to ice-cold N,N-dimethylformamide (50 ml) containing 4.91 g of 4,5-dibromo-2-methylimidazole. The reaction mixture was stirred at room temperature for 1 hour. 2-(Trimethysilyl)ethoxymethyl chloride (3.75 g) was added dropwise to the mixture on ice, and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, ethyl acetate was added to the resulting residue, and the mixture was washed subsequently with a saturated sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica-gel column chromatography (eluent, hexane:ethyl acetate=3:1) to obtain 7.6 g of colorless oily material of 4,5-dibromo-2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)imidazole.

Provenance & Evidence