Sodium hydride → 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile

Participants

Reaction Steps

To a round bottom flask was added NaH (60% in mineral oil) (200 mg, 5.22 mmol) in dry THF (12 ml), followed by the addition of 1H-imidazole-4-carbonitrile (400 mg, 4.3 mmol), SEMCl (1433 mg, 8.6 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc/sat. NaHCO3. The organic phase was separated, washed with water, brine, dried over anhy. Na2SO4, filtered and concentrated. The resulting residue was purified by flash chromatography on silica gel (0-3% MeOH/CH2Cl2). The product fractions were collected and concentrated to afford 355 mg of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile, m/z 224.6 [M+1]+.

Provenance & Evidence