[CH3:1][CH:2]([CH3:22])[C:3]([C:5]1[O:6][C:7]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][S:19][CH2:18][CH2:17]3)=[CH:11][C:8]=2[C:9]=1[CH3:10])=[O:4].[BH4-].[Na+].O>CO.O1CCCC1>[CH3:1][CH:2]([CH3:22])[CH:3]([C:5]1[O:6][C:7]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:17][CH2:18][S:19][CH2:20][CH2:21]3)=[CH:11][C:8]=2[C:9]=1[CH3:10])[OH:4]
2-Methyl-1-[3-methyl-5-(tetrahydro-2H-thiopyran-4-yloxy)-1-benzofuran-2-yl]propan-1-one (849 mg) synthesized above was dissolved in methanol (3 mL)-tetrahydrofuran (15 mL), and sodium tetrahydroborate (90%) (202 mg) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 100:0-85:15, v/v) to give the title compound (621 mg, 73%) as a colorless oil.
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