potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in toluene T=80°C; 2 h;

1: 100 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium(0) / toluene / 2 h / 80 °C 2: 95 percent / 1 N aq. NaOH / tetrahydrofuran; methanol / Ambient temperature 3: 97 percent / triethylamine, 1-ethyl-3-<(dimethylamino)propyl>carbodiimide hydrochloride, hydroxybenzotriazole / CH2Cl2 / 16 h / Ambient temperature 4: 100 percent / LiAlH4 / diethyl ether / 0.33 h / 0 °C 5: 78 percent / CH2Cl2 / 16 h / Ambient temperature 6: 9.5 percent / H2 / 10percent Pd/C / ethanol / 6 h / 2585.7 Torr 7: 95 percent / HCl (gas) / CH2Cl2 / 5 h / Ambient temperature 8: pyridine / CH2Cl2 / 16 h / Ambient temperature 9: toluene / 1 h / 80 °C 10: HCl (gas) / CH2Cl2 / 16 h / Ambient temperature View Scheme