in N,N-dimethyl-formamide

tetrachloromethane; triphenylphosphine in acetonitrile T=20°C; 7 h;

1: 95 percent / lithium aluminium hydride / tetrahydrofuran / 3 h / Heating 2: 90 percent / carbon tetrachloride; triphenylphosphine / acetonitrile / 7 h / 20 °C View Scheme

1: 87 percent / lithium hydroxide monohydrate / tetrahydrofuran / 6 h / Heating 2: 83 percent / copper(I) iodide / methanol; dimethylformamide / 3 h / 90 °C 3: 95 percent / lithium aluminium hydride / tetrahydrofuran / 3 h / Heating 4: 90 percent / carbon tetrachloride; triphenylphosphine / acetonitrile / 7 h / 20 °C View Scheme

1: 83 percent / copper(I) iodide / methanol; dimethylformamide / 3 h / 90 °C 2: 95 percent / lithium aluminium hydride / tetrahydrofuran / 3 h / Heating 3: 90 percent / carbon tetrachloride; triphenylphosphine / acetonitrile / 7 h / 20 °C View Scheme

1: LiAlH4 2: SOCl2 View Scheme

1: (i) OH-, (ii) /BRN= 1098229/, H2SO4 2: LiAlH4 3: SOCl2 View Scheme

1: OH- / Heating 2: (i) OH-, (ii) /BRN= 1098229/, H2SO4 3: LiAlH4 4: SOCl2 View Scheme

1: dimethylformamide 2: NaOEt 3: aq. HCl / acetic acid View Scheme