[H-].[Li+].[Al+3].[H-].[H-].[H-].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:17]=1)[C:11](OC)=[O:12].O.[OH-].[Na+]>O1CCCC1>[OH:12][CH2:11][C:10]1[CH:9]=[C:8]([OH:7])[CH:17]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:15]=1With ice cooling, to a solution of aluminum lithium hydride (1.80 g, 47.5 mmol) in tetrahydrofuran (50 mL) was added dropwise a solution of methyl 3-hydroxy-5-(methoxymethoxy)benzoate (7.74 g, 36.5 mmol) in tetrahydrofuran (50 mL), and the mixture was stirred at room temperature for 4 hours. To the reaction solution were successively added water (2 mL), a 15% aqueous sodium hydroxide solution (2 mL) and water (7 mL), and the mixture was further stirred for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5) to give the title compound (4.46 g, yield 66%) as an oily matter.
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