hydrogen; palladium on activated charcoal in ethanol 5 h; Ambient temperature; Yield given;

1: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 2: 60 percent / phosphorus tribromide / diethyl ether / 3 h / Heating 3: 1.) lithium, ammonia, 2.) dimethylsulfoxide / 2.) THF, a) 2 h, b) 4 h 4: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 5: 76 percent / H2 / Pd/C / ethanol 6: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 2: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme