perchloric acid; hydrogen; palladium on activated charcoal in ethanol T=50°C; P=3620.04 Torr; 3 h;

triethyl phosphite T=170°C; 3 h;

1: 82 percent / H2 / 10percent Pd/C / ethanol / 2 h / 50 °C / 1034.3 Torr 2: 1.) NaH / 1.) pentane, THF, RT, a) 1 h, reflux, b) 1 h, 2.) RT, 3 h 3: 1.) t-BuLi / 1.) THF, -78 deg C, 1 h, 2.) a.) -78 deg C, 10 min, b) RT, 1 h 4: 0.08 g / TFA / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 40 percent / acetic acid / H2O; methanol / 3 h / Heating 2: 82 percent / H2 / 10percent Pd/C / ethanol / 2 h / 50 °C / 1034.3 Torr 3: 1.) NaH / 1.) pentane, THF, RT, a) 1 h, reflux, b) 1 h, 2.) RT, 3 h 4: 1.) t-BuLi / 1.) THF, -78 deg C, 1 h, 2.) a.) -78 deg C, 10 min, b) RT, 1 h 5: 0.08 g / TFA / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 76 percent / CH3COOH / methanol / 4 h / Heating 2: 75 percent / H2, HClO4 / 10percent Pd-C / ethanol / 3 h / 50 °C / 3620.04 Torr View Scheme

trifluoroacetic acid in dichloromethane 4 h; Ambient temperature;

1: 1.) NaH / 1.) pentane, THF, RT, a) 1 h, reflux, b) 1 h, 2.) RT, 3 h 2: 1.) t-BuLi / 1.) THF, -78 deg C, 1 h, 2.) a.) -78 deg C, 10 min, b) RT, 1 h 3: 0.08 g / TFA / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 95 percent / benzene / 3 h / Heating 2: 73 percent / triethyl phosphite / 3 h / 170 °C View Scheme