[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:17]=1.[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]([OH:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:17]=1To a solution of 2.0 g of 3-fluoro-6,11-dihydrodibenz[b,e]oxepin-11-one in 20 ml of methanol is added 0.5 g of sodium borohydride with ice-cooling and then the mixture is stirred at the same temperature for 1 hour. The reaction mixture is poured into water and the resultant is extracted with toluene. The extract is washed with water and then dried over magnesium sulfate. Toluene is distilled off to give 1.9 g of 3-fluoro-6,11-dihydrodibenz[b,e]oxepin-11-ol (crystals). Mass spectrum m/z: 230(M+).
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