lithium aluminium tetrahydride in tetrahydrofuran T=0 - 25°C; 1 h;

1: LAH / tetrahydrofuran / 1 h / 0 - 25 °C 2: VCl3(THF)3, Zn-Cu / CH2Cl2 / 3 h / Ambient temperature 3: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature 4: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating 5: CH2Cl2 / 18 h / Heating 6: NaH / dimethylformamide / 18 h / Ambient temperature 7: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature View Scheme

1: LAH / tetrahydrofuran / 1 h / 0 - 25 °C 2: VCl3(THF)3, Zn-Cu / CH2Cl2 / 3 h / Ambient temperature 3: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature 4: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating 5: CH2Cl2 / 18 h / Heating 6: NaH / dimethylformamide / 18 h / Ambient temperature 7: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature View Scheme

1: LAH / tetrahydrofuran / 1 h / 0 - 25 °C 2: VCl3(THF)3, Zn-Cu / CH2Cl2 / 3 h / Ambient temperature 3: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature 4: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating 5: CH2Cl2 / 18 h / Heating 6: NaH / dimethylformamide / 18 h / Ambient temperature 7: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature View Scheme