hydrogen; 5 percent palladium-carbon; palladium dichloride in ethanol P=750.06 Torr;

1: benzophenone / 9 h / 0 °C / UV-irradiation 2: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme

1: benzophenone / 9 h / 0 °C / UV-irradiation 2: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C View Scheme

1: 1.) n-BuLi / 1.) THF, -78 degC, 3 h; 2.) THF, -78 degC, 0.5 h, allowed to warm to room temp. for 15 h 2: 57 percent / Raney-Ni / ethanol / 6 h / Heating 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme