[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[CH3:14][O:15][CH2:16]Cl.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:14][O:15][CH2:16][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]15 g of Indol-3-aldehyde was dissolved in 40 ml of N,N-dimethylformamide, and 1.38 g of 60% sodium hydride was added under ice-cooling. The reaction solution was stirred for 20 minutes with ice-cooling, then 3.2 ml of chloromethyl methyl ether was added, and stirring was continued at room temperature for 16 hours. The reaction solution was cooled in ice, treated with water and ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography, to give 6.1 g of the title compound (20-44% ethyl acetate-hexane)
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