[BH4-].[Na+].CO.[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]([O:20][CH3:21])=[C:12]2[C:8]=1[CH2:9][CH:10]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[C:11]2=[O:22].Cl>O>[OH:22][CH:11]1[C:12]2[C:8](=[C:7]([O:6][CH3:5])[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]=2[O:20][CH3:21])[CH2:9][CH:10]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1Sodium borohydride (254 mg, 6.72 mmols) was added to a methanol (15 ml) solution of methyl 4-[4-(4,5,6,7-tetramethoxyindan-1-on-2-yl)butoxy]benzoate (1.54 g, 3.36 mmols), with cooling with ice, and then the mixture allowed to warm to room temperature, and stirring was continued for 6 hours. Water was added to the reaction mixture, which was then neutralized with hydrochloric acid added thereto, and thereafter extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo to obtain methyl 4-[4-(1-hydroxy-4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoate (1.50 g).
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