[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[C:20]([C:26](OCC)=[O:27])[C:21]=2[O:22][CH2:23][O:24][CH3:25])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+]>C1COCC1>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[C:20]([CH2:26][OH:27])[C:21]=2[O:22][CH2:23][O:24][CH3:25])=[CH:13][CH:12]=1)([CH3:10])([CH3:8])[CH3:9]To lithium aluminium hydride (27 mg, 0.72 mmol) in THF (0.86 mL), 2-(4-t-butylphenyl)-3-methoxymethyloxy-4-ethoxycarbonylthiophene (0.21 g, 0.60 mmol) in THF (0.86 mL) was added dropwise under cooling with ice, and the reaction solution was stirred under cooling with ice for 1 hour. 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, concentrated and purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to give the desired product as a colorless oil (87 mg, yield 47%).
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