palladium on activated charcoal; hydrogen in ethanol 4 h; Ambient temperature;

1: 1) NaH (80percent in paraffine oil) / 1) anh. THF, 30 min, r. t., 2) THF, 6 h, reflux 2: 88 percent / 0.2N H2SO4 / 16 h / Heating 3: 48 percent / NaH (80percent in paraffine oil) / tetrahydrofuran / 12 h / Heating 4: 97 percent / H2, Pd/C (10percent) / ethanol / 4 h / Ambient temperature View Scheme

1: 81 percent / p-toluenesulfonic acid / benzene / 5 h 2: 1) NaH (80percent in paraffine oil) / 1) anh. THF, 30 min, r. t., 2) THF, 6 h, reflux 3: 88 percent / 0.2N H2SO4 / 16 h / Heating 4: 48 percent / NaH (80percent in paraffine oil) / tetrahydrofuran / 12 h / Heating 5: 97 percent / H2, Pd/C (10percent) / ethanol / 4 h / Ambient temperature View Scheme

1: 48 percent / NaH (80percent in paraffine oil) / tetrahydrofuran / 12 h / Heating 2: 97 percent / H2, Pd/C (10percent) / ethanol / 4 h / Ambient temperature View Scheme

1: 48 percent / NaH (80percent in paraffine oil) / tetrahydrofuran / 12 h / Heating 2: 97 percent / H2, Pd/C (10percent) / ethanol / 4 h / Ambient temperature View Scheme

1: 88 percent / 0.2N H2SO4 / 16 h / Heating 2: 48 percent / NaH (80percent in paraffine oil) / tetrahydrofuran / 12 h / Heating 3: 97 percent / H2, Pd/C (10percent) / ethanol / 4 h / Ambient temperature View Scheme