hydrogen; Pd-BaSO4 in pyridine T=25°C; 4 h;

1: 85 percent / pyridinium p-toluolsulfonate / CH2Cl2 / 4 h / 25 °C 2: n-butyllithium / 1) THF, -78 deg C, 30 min; 2) 25 deg C, 1 h 3: 99 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 °C 4: 92 percent / H2 / 5percent Pd / BaSO4 / pyridine / 4 h / 25 °C View Scheme

1: n-butyllithium / 1) THF, -78 deg C, 30 min; 2) 25 deg C, 1 h 2: 99 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 °C 3: 92 percent / H2 / 5percent Pd / BaSO4 / pyridine / 4 h / 25 °C View Scheme

1: 99 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 °C 2: 92 percent / H2 / 5percent Pd / BaSO4 / pyridine / 4 h / 25 °C View Scheme