Ammonium Chloride → 5-Ethynyl-1-methyl-4-phenyl-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2M in pentane, 650 μL) was added dropwise to trimethylsilyldiazomethane (2M in hexane, 750 μL) in THF (1 mL), cooled to −78° C. and stirred for 30 minutes. 1-Methyl-4-phenyl-1H-imidazole-5-carbaldehyde (intermediate 2) (186 mg) was added dropwise over 5 minutes and stirring continued at −78° C. for 30 minutes, then warmed to 0° C. over 30 minutes and stirred for a further 30 minutes at 0° C. Saturated aqueous ammonium chloride (3 mL) was added, mixture extracted with diethyl ether (3×5 mL), organics combined dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with DCM:MeOH (50.1) afforded the title compound as yellow solid (61.3 mg, 34%);

Provenance & Evidence