Chloromethyl Methyl Ether → HCID 21847951, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-chlorophenyl)-4-(4-pyridyl) imidazole from Step A (200 mg, 0.78 mmol) in THF (8 mL) at room temperature was added sodium hydride (63 mg of a 60% oil dispersion, 1.57 mmol). After cooling to 0° C., methoxymethyl chloride (74 μL, 0.97 mmol) was slowly added. The reaction was stirred at 0 oC for 1 h, then at room temperature for 1 h. The reaction was quenched by the addition of 5% sodium bicarbonate solution and the mixture was extracted with ethyl acetate (2 times). The combined extracts were successively washed with 5% sodium bicarbonate solution, water and saturated salt solution and dried over anhydrous sodium sulfate. The solution was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-3% methanol in methylene chloride to yield the title compound as a pale yellow solid (172 mg, 72% yield), mass spectrum (CI) m/e=300 (M+1)+.

Provenance & Evidence