lithium aluminium tetrahydride in tetrahydrofuran T=0 - 5°C; 3 h;

1: 89 percent / Et3N / ethanol / 4 h / Heating 2: 65 percent / hydrazine hydrate / Raney-Ni / ethanol; 1,2-dichloro-ethane / 4 h / 60 °C 3: 78 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 90 °C 4: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature 5: 85 percent / Ac2O / Ambient temperature 6: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 5 °C View Scheme

1: 92 percent / CuCl2, tert-butylnitrite / acetonitrile / 2 h / 65 °C 2: 89 percent / Et3N / ethanol / 4 h / Heating 3: 65 percent / hydrazine hydrate / Raney-Ni / ethanol; 1,2-dichloro-ethane / 4 h / 60 °C 4: 78 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 90 °C 5: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature 6: 85 percent / Ac2O / Ambient temperature 7: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 5 °C 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

1: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature 2: 85 percent / Ac2O / Ambient temperature 3: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 5 °C View Scheme

1: 65 percent / hydrazine hydrate / Raney-Ni / ethanol; 1,2-dichloro-ethane / 4 h / 60 °C 2: 78 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 90 °C 3: 90 percent / H2 / Raney-Ni / ethanol; H2O / 1 h / 760 Torr / Ambient temperature 4: 85 percent / Ac2O / Ambient temperature 5: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 5 °C View Scheme

1: 85 percent / Ac2O / Ambient temperature 2: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 5 °C View Scheme