1: 78 percent / CHCl3 / 1.5 h / Ambient temperature 2: 96 percent / ethanol; CHCl3; diethyl ether / 1 h / 0 °C 3: 1.) LiAlH4, 2.) NaBH4 / 1.) THF, Et2O, reflux, 3 h, 2.) MeOH, overnight 4: pyridine / 3 h / Ambient temperature 5: LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Heating View Scheme

1: pyridine / 3 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Heating View Scheme

1: 96 percent / ethanol; CHCl3; diethyl ether / 1 h / 0 °C 2: 1.) LiAlH4, 2.) NaBH4 / 1.) THF, Et2O, reflux, 3 h, 2.) MeOH, overnight 3: pyridine / 3 h / Ambient temperature 4: LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Heating View Scheme

1: 1.) LiAlH4, 2.) NaBH4 / 1.) THF, Et2O, reflux, 3 h, 2.) MeOH, overnight 2: pyridine / 3 h / Ambient temperature 3: LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Heating View Scheme

1: n-butyl nitrite, HCl / acetic acid 2: 1) PCl5, 2) KOH / 1) ether, 2) MeOH 3: 95 percent / 0.5 N NaOH, H2 / 10 percent Pd/C / 3 h / 2327.2 Torr 4: 2.7 g / acetyl chloride / 2 h / Heating 5: 1,2-dichloro-ethane / 0.5 h / Ambient temperature; other temp, other solvents 6: 3 g / methanol; CHCl3 / 2 h / 0 °C 7: 600 mg / LAH / tetrahydrofuran / 6 h / Ambient temperature 8: 690 mg / pyridine / 16 h / 5 °C 9: 420 mg / LAH / tetrahydrofuran / 6 h / Heating View Scheme

1: 67 percent / P2O5 / benzene / 2 h / Heating 2: n-butyl nitrite, HCl / acetic acid 3: 1) PCl5, 2) KOH / 1) ether, 2) MeOH 4: 95 percent / 0.5 N NaOH, H2 / 10 percent Pd/C / 3 h / 2327.2 Torr 5: 2.7 g / acetyl chloride / 2 h / Heating 6: 1,2-dichloro-ethane / 0.5 h / Ambient temperature; other temp, other solvents 7: 3 g / methanol; CHCl3 / 2 h / 0 °C 8: 600 mg / LAH / tetrahydrofuran / 6 h / Ambient temperature 9: 690 mg / pyridine / 16 h / 5 °C 10: 420 mg / LAH / tetrahydrofuran / 6 h / Heating View Scheme

1: 1) PCl5, 2) KOH / 1) ether, 2) MeOH 2: 95 percent / 0.5 N NaOH, H2 / 10 percent Pd/C / 3 h / 2327.2 Torr 3: 2.7 g / acetyl chloride / 2 h / Heating 4: 1,2-dichloro-ethane / 0.5 h / Ambient temperature; other temp, other solvents 5: 3 g / methanol; CHCl3 / 2 h / 0 °C 6: 600 mg / LAH / tetrahydrofuran / 6 h / Ambient temperature 7: 690 mg / pyridine / 16 h / 5 °C 8: 420 mg / LAH / tetrahydrofuran / 6 h / Heating View Scheme

1: 95 percent / 0.5 N NaOH, H2 / 10 percent Pd/C / 3 h / 2327.2 Torr 2: 2.7 g / acetyl chloride / 2 h / Heating 3: 1,2-dichloro-ethane / 0.5 h / Ambient temperature; other temp, other solvents 4: 3 g / methanol; CHCl3 / 2 h / 0 °C 5: 600 mg / LAH / tetrahydrofuran / 6 h / Ambient temperature 6: 690 mg / pyridine / 16 h / 5 °C 7: 420 mg / LAH / tetrahydrofuran / 6 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether 3 h; Heating; Yield given;

1: 78 percent / CHCl3 / 1.5 h / Ambient temperature 2: 96 percent / ethanol; CHCl3; diethyl ether / 1 h / 0 °C 3: 1.) LiAlH4, 2.) NaBH4 / 1.) THF, Et2O, reflux, 3 h, 2.) MeOH, overnight 4: pyridine / 3 h / Ambient temperature 5: LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Heating View Scheme