methanol; pyridinium p-toluenesulfonate in dichloromethane T=0 - 5°C;

1: 1.) NaH / 1.) THF, 50-55 deg C, 30 min, 2.) THF, reflux, 8 h 2: 82 percent / H2 / 10percent Pd/C / methanol; CHCl3 / 12 h / Ambient temperature 3: 93.5 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH2Cl2; dimethylformamide / 24 h / Ambient temperature 4: 60 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH2Cl2 / 96 h / Ambient temperature 5: 75 percent / pyridinium p-toluenesulfonate, MeOH / CH2Cl2 / 0 - 5 °C View Scheme

1: 82 percent / H2 / 10percent Pd/C / methanol; CHCl3 / 12 h / Ambient temperature 2: 93.5 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH2Cl2; dimethylformamide / 24 h / Ambient temperature 3: 60 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH2Cl2 / 96 h / Ambient temperature 4: 75 percent / pyridinium p-toluenesulfonate, MeOH / CH2Cl2 / 0 - 5 °C View Scheme

1: 93.5 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH2Cl2; dimethylformamide / 24 h / Ambient temperature 2: 60 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH2Cl2 / 96 h / Ambient temperature 3: 75 percent / pyridinium p-toluenesulfonate, MeOH / CH2Cl2 / 0 - 5 °C View Scheme

1: 60 percent / 4-(N,N-dimethylamino)pyridine, DCC / CH2Cl2 / 96 h / Ambient temperature 2: 75 percent / pyridinium p-toluenesulfonate, MeOH / CH2Cl2 / 0 - 5 °C View Scheme