lithium aluminium tetrahydride in tetrahydrofuran 3 h; Heating;

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating;

1: tetrahydrofuran / 0.5 h / 60 °C 2: TsOH / benzene / 4 h / Heating 3: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 4: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 5: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 6: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 7: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 8: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: dichlorobis(triphenylphosphine)nickel(II) / tetrahydrofuran / 24 h / Ambient temperature 2: H2, conc. HCl / PtO2 / methanol / 2585.7 Torr 3: Et3N / toluene / 0.5 h / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

1: H2, conc. HCl / PtO2 / methanol / 2585.7 Torr 2: Et3N / toluene / 0.5 h / Ambient temperature 3: LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

in chloroform

1: 10.83 g / H2O; dioxane / 10 h / Heating 2: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 3: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 4: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 5: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 6: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 7: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 2: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 3: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 4: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 5: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 6: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 2: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 3: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 4: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 5: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 6: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: TsOH / benzene / 4 h / Heating 2: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 3: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 4: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 5: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 6: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 7: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme