lithium aluminium tetrahydride in tetrahydrofuran 24 h; Heating;

1.1: C2H5ONa / ethanol / 1 h / Heating 1.2: 61 percent / ethanol / 4 h / Heating 2.1: 70 percent / H2; aq. HCl / Pd/C / methanol / 72 h / 36775.4 Torr 3.1: BH3*THF / tetrahydrofuran / 8 h / Heating View Scheme

1: 70 percent / H2; aq. HCl / Pd/C / methanol / 72 h / 36775.4 Torr 2: BH3*THF / tetrahydrofuran / 8 h / Heating View Scheme

1: HBr (gas) / CH2Cl2; diethyl ether 2: dimethylformamide; H2O / Heating 3: 79 percent / LiAlH4 / tetrahydrofuran / 24 h / Heating View Scheme

borane-THF in tetrahydrofuran 8 h; Heating;