1: 78 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 90 °C 2: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature View Scheme

1: 78 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 90 °C 2: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature 3: 85 percent / Ac2O / Ambient temperature 4: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 5 °C View Scheme

With  hydrazine hydrate; nickel in  ethanol; 1,2-dichloro-ethane T=60°C; 4 h;   

With  [Cu(CH3CN)4]BF4 in  toluene T=90°C; 20 h;   

Multi-step reaction with 3 steps 1: 78 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 90 °C2: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature3: 85 percent / Ac2O / Ambient temperature