[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].C([O:13][C:14]([C:16]1[C:25]([Br:26])=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)=O)C.O.N>O1CCCC1>[Br:26][C:25]1[C:16]([CH2:14][OH:13])=[CH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2To the mixture of lithium aluminum hydride (430 mg, 9.0 mmol) and tetrahydrofuran (15 ml) under nitrogen atmosphere, aluminum chloride (1.7 g, 13 mmol) was added at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at the same temperature for 1 hour. Subsequently, 3-bromo-naphthalene-2-carboxylic acid ethyl ester (500 mg, 1.8 mmol) was added to the reaction mixture at 0° C. (an outer temperature), and the reaction mixture was stirred at the same temperature for 1.5 hours. 28% ammonia water was added to the reaction mixture, followed by filtration with Celite. The solvents were evaporated under reduced pressure from the filtrate, and then the obtained residue was purified with NH-silica gel column chromatography (heptane:ethyl acetate=3:1), thereby obtaining the entitled compound (280 mg, 67%).
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