1: 76.5 percent / H2 / Raney nickel / acetic acid; methanol; H2O / 2 h 2: 89 percent / aluminum oxide / benzene / 0.25 h / Heating 3: 94 percent / cerium(III) chloride heptahydrate, sodium borohydride / methanol / 0.17 h / Ambient temperature 4: 42 percent / aluminum oxide / toluene / 0.5 h / Heating 5: 77 percent / p-toluenesulfonic acid monohydrate / methanol / 12 h / Ambient temperature 6: 75 percent / 1,3-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 72 h / Ambient temperature 7: 10percent aq. HCl / tetrahydrofuran / 4 h / 50 °C 8: pyridinium chlorochromate, aluminum oxide / CH2Cl2 / 8 h / Ambient temperature 9: 30 percent / hydrofluoric acid / acetonitrile; H2O / 8 h / 45 °C View Scheme