[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:8][O:9][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:19]I.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[C:7]([CH:10]([CH3:19])[C:11]([O:13][CH3:14])=[O:12])=[N:8][O:9][C:5]=2[CH:4]=1To a solution of methyl (6-methoxy-1,2-benzisoxazol-3-yl)acetate (3.00 g, 13.6 mmol) in anhydrous THF (70 mL) was added 60% sodium hydride (544 mg, 13.6 mmol) under ice-cooling. After stirring for 30 min, methyl iodide (0.929 mL, 14.9 mmol) in THF (4 mL) was added dropwise thereto, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. This solution was applied to basic silica gel column chromatography (ethyl acetate) to give the title compound (3.19 g, quantitative) as an oil.
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