potassium carbonate in N,N-dimethyl-formamide T=50°C;

potassium carbonate; sodium iodide in N,N-dimethyl-formamide T=0 - 20°C; 4.5 h;

1: 98 percent / tetrahydrofuran / Ambient temperature 2: 71 percent / K2CO3 / acetone / Heating View Scheme

hydrogen; palladium on activated charcoal in ethyl acetate 0.5 h;

1: 71 percent / diisobutylaluminum hydride / toluene / 1 h / 45 °C 2: 86 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 98 percent / hydrogen / palladium on carbon / ethyl acetate / 0.5 h 2: 48 percent / potassium carbonate; sodium iodide / dimethylformamide / 4.5 h / 0 - 20 °C 3: pyridine / 2 h / cooling 4: 1.55 g / potassium carbonate / tetrakis(triphenylphosphine)palladium(0) / benzene; ethanol / 14 h / Heating View Scheme

1: 98 percent / hydrogen / palladium on carbon / ethyl acetate / 0.5 h 2: 48 percent / potassium carbonate; sodium iodide / dimethylformamide / 4.5 h / 0 - 20 °C View Scheme