1: 1.) NaH, 2.) Ag2O, MgSO4 / 1.) THF, 0 deg C, 30 min, 2.) THF, 1.5 h 2: 83 percent / p-toluenesulfonic acid / xylene / 1.25 h / Heating 3: 99 percent / H2 / 10percent Pd/C / ethanol / 1 h / Ambient temperature View Scheme

1: 1.) NaH, 2.) Ag2O, MgSO4 / 1.) THF, 0 deg C, 30 min, 2.) THF, 1.5 h 2: 83 percent / p-toluenesulfonic acid / xylene / 1.25 h / Heating View Scheme