1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 2: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 3: methanol / 1.17 h / 70 °C 4: 5.5 g / NaBH4 / methanol / 1.17 h / 0 - 20 °C 5: 97 percent / 6 h / Heating 6: 35.5 percent / phenyliodine(III) diacetate / 0.67 h / 20 °C 7: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 8: 98 percent / pyridine / 1 h / 0 °C 9: 97 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 3 h / 60 °C 10: lithium tri-sec-butylborohydride / tetrahydrofuran / 6 h / -78 °C 11: 23.4 mg / lithium aluminum hydride / tetrahydrofuran / 12 h / 20 °C View Scheme

diisobutylaluminium hydride in hexane; toluene T=-78°C; 15-20 min;

1: 95 percent / LiAlH4 / tetrahydrofuran / 0.67 h / 25 °C 2: 90 percent / MnO2 / CH2Cl2 / 2 h / 25 °C / other reagent View Scheme

1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 2: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 3: methanol / 1.17 h / 70 °C 4: 5.5 g / NaBH4 / methanol / 1.17 h / 0 - 20 °C 5: 97 percent / 6 h / Heating 6: 35.5 percent / phenyliodine(III) diacetate / 0.67 h / 20 °C 7: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 8: 98 percent / pyridine / 1 h / 0 °C 9: 97 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 3 h / 60 °C 10: 92 percent / pyridinium p-toluenesulfonate / benzene / 48 h / Heating 11: lithium aluminum hydride / tetrahydrofuran / 24 h 12: 20.6 mg / aq. HCl / tetrahydrofuran / 24 h / 20 °C View Scheme

sodium hydroxide in tetrahydrofuran; water

1: 4.25 g / LiAlH4 / tetrahydrofuran / 0.5 h 2: 3.9 g / active MnO2 / CHCl3 / 0.5 h / Heating 3: 2.47 g / 50percent aqueous KOH / methanol / 5 h / Heating 4: 1) thallium(III) nitrate / methanol / 1) 1 h, 2) 3 h 5: 190 mg / aqueous HCl / methanol / 4 h / Heating 6: 10 mg / concentrated HCl / acetic acid / 1 h / water-bath View Scheme