Methyl iodide → 5-[2-(2-Chloro-4-methoxy-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one

Participants

Reaction Conditions

Reaction Steps

5-[2-(2-Chloro-4-methoxy-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one (2.45 g) was dissolved in DMF (60 mL). The mixture was cooled to 0° C. To this solution was added sodium hydride (55% in mineral oil, 403 mg) over a period of 10 minutes. The mixture was stirred for 10 minutes at 0° C. and then for 1 hour at r.t. The mixture was cooled to 0° C. and methyl iodide (0.49 mL) was added dropwise over a period of 10 minutes. Stirring was continued for 1.5 hours at r.t. The reaction mixture was poured into ice/water and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a light brown foam (1.99 g, 76%). MS (m/e)=346.1 [M+H+].

Provenance & Evidence