Dimethyl Sulfate → 1-methyl-2-phenyl-1H-imidazole-5-carbaldehyde

Participants

Reaction Steps

To a solution of 4-formyl-2-phenylimidazole (100 mg, 0.58 mmol) in CH2Cl2 (2 mL) was added aqueous KOH (2 mL of a 30% solution), followed by dimethyl sulfate (66 μL, 0.70 mmol), and tetrabutylammonium bromide (10 mg; 0.039 mmol). The reaction mixture was stirred overnight at RT and then was partitioned between ETOAc and water; the organic phase was washed with brine and then concentrated in vacuo. The residue was chromatographed (SiO2; continuous gradient from 1:1 hexane:EtOAc to 100% EtOAc) to give 1-methyl-2-phenyl-imidazole-5-carboxaldehyde as a solid (35 mg; 32%; 1st eluted fraction; Part A compound) and Part B compound

Provenance & Evidence