[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])=[O:7])(C)(C)[CH3:2].[H-].[Na+].BrCCO.C(OCC)(=O)C>CN(C)C=O>[O:7]=[C:6]1[N:8]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH2:2][CH2:1][O:5]1
To a solution of 2.93 g of 3-[N-(t-butoxycarbonyl)amino]benzaldehyde in 20 ml of dimethylformamide was added 0.58 g of sodium hydride (60% oily) under ice-cooling. After stirring at room temperature for 1 hour, a solution of 0.93 ml of 2-bromoethanol in 5 ml of dimethylformamide was added dropwise under ice-cooling. After stirring at room temperature for 14 hours, the mixture was heated to stir at 115° C. for 6 hours. Ethyl acetate was added, and this was washed successively with water and an aqueous saturated sedum chloride solution, dried with anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.75 g of oily 3-(2-oxo-oxazolidin-3-yl)benzaldehyde.
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