[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[O-]CC.[Na+].[CH3:14][C:15]1[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1.[Cl-].[NH4+]>CO.O>[N:1]([C:4](=[CH:20][C:18]1[S:19][C:15]([CH3:14])=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]To a solution of ethyl azidoacetate (10.6 g) in methanol (65 mL) was added sodium ethoxide (20% solution in ethanol, 27.2 g) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. 5-Methylthiophene-2-carbaldehyde (2.5 g) was added to this solution and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added saturated ammonium chloride aqueous solution and water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0−90/10) to give the title compound (3.39 g)
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