1: p-toluenesulfonic acid / benzene / 16.5 h / Heating 2: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature View Scheme

1: p-toluenesulfonic acid / benzene / 16.5 h / Heating 2: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 3: 60 percent / phosphorus tribromide / diethyl ether / 3 h / Heating 4: 1.) lithium, ammonia, 2.) dimethylsulfoxide / 2.) THF, a) 2 h, b) 4 h 5: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 6: 76 percent / H2 / Pd/C / ethanol 7: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: p-toluenesulfonic acid / benzene / 16.5 h / Heating 2: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 3: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme