sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran; toluene T=-10°C; 48 h;

lithium aluminium tetrahydride in diethyl ether 4 h; Ambient temperature;

1: With oxygen; ozone; acetic acid in dichloromethane T=0°C; 2: With sodium tris(acetoxy)borohydride in dichloromethane T=0 - 20°C; Further stages.;

2: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: 10N aq. NaOH / ethanol / 0.5 h / Ambient temperature 3: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: pyridine / Ambient temperature 2: aq. NaIO4, RuCl3 / acetonitrile; CCl4 / 8 h / Ambient temperature 3: 10N aq. NaOH / ethanol / 0.5 h / Ambient temperature 5: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: 10N aq. NaOH / ethanol 3: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / Ambient temperature 4: 100 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 5: 91 percent / pyridine / 5 h 6: 1.) CuI / 1.) Et2O, -10 deg C, 30 min, 2.) Et2O, 0 deg C, 2 h 7: pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 8: pyridine / Ambient temperature 9: aq. NaIO4, RuCl3 / acetonitrile; CCl4 / 8 h / Ambient temperature 10: 10N aq. NaOH / ethanol / 0.5 h / Ambient temperature 12: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: aq. NaIO4, RuCl3 / acetonitrile; CCl4 / 8 h / Ambient temperature 2: 10N aq. NaOH / ethanol / 0.5 h / Ambient temperature 4: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / Ambient temperature 2: 100 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 3: 91 percent / pyridine / 5 h 4: 1.) CuI / 1.) Et2O, -10 deg C, 30 min, 2.) Et2O, 0 deg C, 2 h 5: pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 6: pyridine / Ambient temperature 7: aq. NaIO4, RuCl3 / acetonitrile; CCl4 / 8 h / Ambient temperature 8: 10N aq. NaOH / ethanol / 0.5 h / Ambient temperature 10: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1.1: 50 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / 20 °C 2.1: 87 percent / NaH / dimethylformamide / 6 h / 20 °C 3.1: O3; O2; MeOH / CH2Cl2 / 0 °C 3.2: 95 percent / NaBH4 / CH2Cl2 / 3 h / 20 °C 4.1: NaNO2; H2SO4 / H2O / 0 °C 5.1: 0.02 g / benzene / 1.5 h / 27 °C / UV-irradiation View Scheme