Water → HCID 22934068, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[3-methoxy-4-(methoxymethoxy)phenyl]-2,2-dimethylpropanamide (500 mg, 1.87 mmol) in tetrahydrofuran (10 ml) was added dropwise 1.59M-n-butyllithium (2.94 ml, 4.68 mmol) at −15° C., and the resulting mixture was slowly warmed up to 0° C. After 2 hours, a solution of methyl iodide (0.175 ml, 2.81 mmol) in tetrahydrofuran (0.5 ml) was added dropwise thereto. After 1 hour, the resulting mixture was warmed up to room temperature. After 14 hours, the reaction solution was poured into water (50 ml) and extracted with ethyl acetate (30 ml×3), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain N-[3-methoxy-4-(methoxymethoxy)-2-methylphenyl]-2,2-dimethylpropanamide (424 mg, 81%).

Provenance & Evidence