hydrogen; palladium on activated charcoal in ethanol 1.5 h;

1: 94 percent / toluene / 20 h / Heating 2: 80 percent / CH2Cl2 / 168 h / Heating 3: 76 percent / aq. HCl / ethanol / 5 h / 20 °C 4: H2O / 2 h / 20 °C 5: 9.3 mg / Et3SiH; CF3CO2H / CH2Cl2 / 0.5 h / Heating 6: 54 percent / H2 / Pd/C / aq. ethanol / 1.5 h View Scheme

1: H2O / 2 h / 20 °C 2: 9.3 mg / Et3SiH; CF3CO2H / CH2Cl2 / 0.5 h / Heating 3: 54 percent / H2 / Pd/C / aq. ethanol / 1.5 h View Scheme

1: 9.3 mg / Et3SiH; CF3CO2H / CH2Cl2 / 0.5 h / Heating 2: 54 percent / H2 / Pd/C / aq. ethanol / 1.5 h View Scheme

MoO5*pyridine*HMPA; lithium diisopropyl amide 1.) THF, hexane, -78 deg C, 2.) a) from -78 to 0 deg C, 15 min, b) from 0 to 10 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: DEAD; PPh3 / toluene / 0.08 h / 20 °C 2: 6.0 mg / NaOH / methanol / 0.25 h / 20 °C View Scheme

triphenylphosphine; diethylazodicarboxylate in toluene T=20°C; Mitsunobu reaction; 0.0833333 h;