1: aq. HCl / 1) 65 - 70 deg C, 4 h, 2) rt, 16 h 2: 97 percent / anh. hydrogen fluoride / 18 h / Ambient temperature View Scheme

1: 10.33 g / LiAlH4 / tetrahydrofuran / 1) 1 h, ice-bath, 2) 1 h, 25 deg C, 3) 1.5 h, 60 deg C 2: 98 percent / imidazole / dimethylformamide / 18 h / ice-bath temp. to r.t. 3: 97 percent / Et3N / CH2Cl2 / 0.25 h / 0 °C 4: 1) CuCN / 1) Et2O, a) -20 deg C, 20 min, b) 0 deg C, 30 min, 2) Et2O, a) -25 deg C, 18 h, b) r.t., 5.5 h 5: 91 percent / AcOH, water / tetrahydrofuran / 24 h / Ambient temperature 6: 95 percent / Jones reagent / acetone / 2 h / Ambient temperature 7: CF3SO3H / benzene / 2 h / 70 °C View Scheme

1: 10.33 g / LiAlH4 / tetrahydrofuran / 1) 1 h, ice-bath, 2) 1 h, 25 deg C, 3) 1.5 h, 60 deg C 2: 98 percent / imidazole / dimethylformamide / 18 h / ice-bath temp. to r.t. 3: 97 percent / Et3N / CH2Cl2 / 0.25 h / 0 °C 4: 1) CuCN / 1) Et2O, a) -20 deg C, 20 min, b) 0 deg C, 30 min, 2) Et2O, a) -25 deg C, 18 h, b) r.t., 5.5 h 5: 91 percent / AcOH, water / tetrahydrofuran / 24 h / Ambient temperature 6: 95 percent / Jones reagent / acetone / 2 h / Ambient temperature 7: CF3SO3H / benzene / 2 h / 70 °C View Scheme

1: aq. HCl / 1) 65 - 70 deg C, 4 h, 2) rt, 16 h 2: 91 percent / AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 10.33 g / LiAlH4 / tetrahydrofuran / 1) 1 h, ice-bath, 2) 1 h, 25 deg C, 3) 1.5 h, 60 deg C 2: 98 percent / imidazole / dimethylformamide / 18 h / ice-bath temp. to r.t. 3: 97 percent / Et3N / CH2Cl2 / 0.25 h / 0 °C 4: 1) CuCN / 1) Et2O, a) -20 deg C, 20 min, b) 0 deg C, 30 min, 2) Et2O, a) -25 deg C, 18 h, b) r.t., 5.5 h 5: 91 percent / AcOH, water / tetrahydrofuran / 24 h / Ambient temperature 6: 95 percent / Jones reagent / acetone / 2 h / Ambient temperature 7: CF3SO3H / benzene / 2 h / 70 °C View Scheme

hydrogenchloride 1) 65 - 70 deg C, 4 h, 2) rt, 16 h; Yield given;