hydrogen; palladium on activated charcoal in diethylene glycol dimethyl ether T=150°C; 1 h;

hydrogen; palladium on activated charcoal in various solvent(s) T=140°C; 2 h;

lithium iodide in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=100°C; 25 h;

1: 73 percent / (CF3CO)2O / CH2Cl2 / 4 h / Ambient temperature 2: 87 percent / hydrogen, conc. HCl / 10percent Pd/C / ethyl acetate 3: 75 percent / K3<Fe(CN)6>, K2CO3 / H2O / 0.17 h 4: hexamethylenetetramine / 1.) reflux, 24h, 2.) water, 60 deg C, 5h 5: 53 percent / BCl3 / CH2Cl2 / 3 h / Ambient temperature 6: 4 percent / LiI / hexamethylphosphoric acid triamide / 25 h / 100 °C View Scheme

1: 87 percent / hydrogen, conc. HCl / 10percent Pd/C / ethyl acetate 2: 75 percent / K3<Fe(CN)6>, K2CO3 / H2O / 0.17 h 3: hexamethylenetetramine / 1.) reflux, 24h, 2.) water, 60 deg C, 5h 4: 53 percent / BCl3 / CH2Cl2 / 3 h / Ambient temperature 5: 4 percent / LiI / hexamethylphosphoric acid triamide / 25 h / 100 °C View Scheme

1: 96 percent / 1,2-dimethoxy-ethane / 2 h / Heating 2: 74 percent / hydrogen / 10percent palladium on carbon / various solvent(s) / 2 h / 140 °C View Scheme

1: hexamethylenetetramine / 1.) reflux, 24h, 2.) water, 60 deg C, 5h 2: 53 percent / BCl3 / CH2Cl2 / 3 h / Ambient temperature 3: 4 percent / LiI / hexamethylphosphoric acid triamide / 25 h / 100 °C View Scheme

1: 75 percent / K3<Fe(CN)6>, K2CO3 / H2O / 0.17 h 2: hexamethylenetetramine / 1.) reflux, 24h, 2.) water, 60 deg C, 5h 3: 53 percent / BCl3 / CH2Cl2 / 3 h / Ambient temperature 4: 4 percent / LiI / hexamethylphosphoric acid triamide / 25 h / 100 °C View Scheme

1: 53 percent / BCl3 / CH2Cl2 / 3 h / Ambient temperature 2: 4 percent / LiI / hexamethylphosphoric acid triamide / 25 h / 100 °C View Scheme

lithium iodide in N,N,N',N',N'',N''-hexamethylphosphoric triamide 40 h; Heating;