m-Chloroperbenzoic acid → HCID 67323290, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro perbenzoic acid (mCPBA) (230 mg, 1.026 mmol) was added to a stirred, cooled 0° C. mixture of 5-(chloromethyl)-2-methoxypyridine (U1) (147 mg, 0.933 mmol) in CH2Cl2 (3731 μl). The reaction mixture was stirred at room temperature for 2 h. Another portion of mCPBA (150 mg) was added and stirred at room temperature for 4 h. A third portion mCPBA (150 mg) was added and the reaction was allowed to stir overnight. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel flash chromatography (first 0-30% EtOAc in hexanes to remove mCPBA and SM, then 0-20% MeOH in CH2Cl2 to wash product out) to provide 5-(chloromethyl)-2-methoxypyridine 1-oxide (U2) as a white solid. ES-MS [M+1]+: 174.1.

Provenance & Evidence