[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:20](=O)[C:19]3=[CH:22][C:23](OCCCCC)=[CH:24][CH:25]=[C:18]3[C:17]2=O)=[CH:10][CH:9]=1.Cl>C1COCC1>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[CH2:20][C:19]3[C:18](=[CH:25][CH:24]=[CH:23][C:22]=3[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:17]2)=[CH:10][CH:9]=1A suspension of LAH (40 mg, 1.1 mmol) in THF (1 ml) was added to a solution of N-2-(4-hydroxyphenyl)ethyl-4-pentyloxyphthalimide (208 mg, 0.59 mmol) in THF (1 ml) at 0° C. The mixture was stirred at room temperature for 3.5 hours. This reaction mixture was poured into a 3N aqueous hydrochloric acid solution (20 ml). The mixture was extracted with ethyl acetate (20 ml×3), and washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (30 ml). The organic layer was dried over anhydrous magnesium sulfate. The drying agent was filtered of, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=30/1) to give N-2-(4-hydroxyphenyl)ethyl-4-pentyloxyisoindoline (181 mg, 94%) as colorless crystals.
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