C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][OH:23])=[O:17].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23])=[O:17]
To a mixture of 13 ml of oxalyl chloride and 400 ml of dichloromethane was added dropwise a solution of 23 ml of dimethyl sulfoxide in 40 ml of dichloromethane at −60° C. for 15 minutes. After stirred at −60° C. for 10 minutes, a solution of 30.2 g of 3-[(2-methoxyethoxy)carbonylamino]benzyl alcohol in 100 ml of dichloromethane was added dropwise at −60° C. for 25 minutes. After stirred at −60° C. for 20 minutes, 56 ml of triethylamine was added dropwise at −60° C. for 15 minutes. After stirred at room temperature for 45 minutes, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed successively with water and then an aqueous saturated sodium chloride solution. After dried over anhydrous magnesium sulfate and then concentration, the resulting crude crystals were washed with t-butyl methyl ether and then dried to obtain 17.55 g of 3-[(2-methoxyethoxy)carbonylamino]benzaldehyde [Compound No. (h)] as a white solid.
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