1: 65 percent / phosphorus pentachloride / CH2Cl2 / 7 h / Heating 2: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 45 min, 2.) THF, hexane, -70 deg C, 2 h 3: 52 percent / H2 / 10percent Pd/C / aq. ethanol / 760 Torr / Ambient temperature View Scheme

1: 65 percent / phosphorus pentachloride / CH2Cl2 / 7 h / Heating 2: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 45 min, 2.) THF, hexane, -70 deg C, 2 h View Scheme

phosphorus pentachloride in dichloromethane T=40°C; 24 h;

thionyl chloride