[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]=2[OH:18])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:24][O:25][CH2:26]Cl.[Cl-].[NH4+]>CN(C)C=O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]=2[O:18][CH2:24][O:25][CH3:26])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]60% Sodium hydride (28 mg, 0.69 mmol) was added to a solution of 2-(4-t-butylphenyl)-3-hydroxy-4-ethoxycarbonylthiophene (0.20 g, 0.66 mmol) obtained in accordance with JP-A-48-26755 in dimethylformamide (1.0 mL) at room temperature, and the reaction solution was stirred at 60° C. for 15 minutes. After the reaction solution was cooled to room temperature, chloromethyl methyl ether (0.055 mL, 0.73 mmol) was added dropwise, and the reaction solution was stirred at room temperature for another 5 hours. After addition of saturated aqueous ammonium chloride, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate. The organic layer was concentrated and purified by silica gel column chromatography (chloroform) to give the desired product as a colorless oil (212 mg, yield 91%).
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