hydrogen; palladium on activated charcoal in ethyl acetate 4 h;

1: SOCl2 / 2 h / Heating 2: NEt3; DMAP / CH2Cl2 / 12 h / 20 °C 3: 92 percent / H2 / Pd/C / ethyl acetate / 4 h View Scheme

1: K2CO3 / acetone / 72 h / Heating 2: SOCl2 / 2 h / Heating 3: NEt3; DMAP / CH2Cl2 / 12 h / 20 °C 4: 92 percent / H2 / Pd/C / ethyl acetate / 4 h View Scheme

1: K2CO3 / acetone / 72 h / Heating 2: SOCl2 / 2 h / Heating 3: NEt3; DMAP / CH2Cl2 / 12 h / 20 °C 4: 92 percent / H2 / Pd/C / ethyl acetate / 4 h View Scheme

1: NEt3; DMAP / CH2Cl2 / 12 h / 20 °C 2: 92 percent / H2 / Pd/C / ethyl acetate / 4 h View Scheme

1: sulfuric acid / 6 h / Reflux 2: potassium carbonate; sodium iodide / acetone / Reflux 3: ethanol; potassium hydroxide / 6 h / Reflux 4: thionyl chloride / 3 h / Reflux 5: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 20 °C 6: palladium on carbon; hydrogen / ethyl acetate / 20 °C View Scheme

1: potassium carbonate; sodium iodide / acetone / Reflux 2: ethanol; potassium hydroxide / 6 h / Reflux 3: thionyl chloride / 3 h / Reflux 4: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 20 °C 5: palladium on carbon; hydrogen / ethyl acetate / 20 °C View Scheme

1: ethanol; potassium hydroxide / 6 h / Reflux 2: thionyl chloride / 3 h / Reflux 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 20 °C 4: palladium on carbon; hydrogen / ethyl acetate / 20 °C View Scheme