1: dimethylformamide 2: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / Heating 3: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

thionyl chloride; N,N-dimethyl-formamide in dichloromethane T=20°C; 2 h;

1: lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 2: thionyl chloride View Scheme

1: tetra-(n-butyl)ammonium iodide; potassium carbonate / 1,4-dioxane / 24 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C View Scheme

1: tetra-(n-butyl)ammonium iodide; potassium carbonate / 1,4-dioxane / 24 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C View Scheme

1: 88 percent / potassium carbonate, potassium iodide / acetone / 18 h / Heating 2: lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 3: thionyl chloride View Scheme