1: hydrogenchloride; palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 5 h / 20 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 °C 3: AlCl3, aluminium chloride / chloroform / 0.5 h / 0 °C 4: sodium tetrahydroborate; sodium hydroxide / water / 72 h / 20 °C 5: triethylsilane; trifluoroacetic acid / 16 h / 20 °C View Scheme

1: hydrogenchloride; palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 5 h / 20 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 °C 3: AlCl3, aluminium chloride / chloroform / 0.5 h / 0 °C View Scheme

hydrogenchloride; palladium 10 on activated carbon; hydrogen in tetrahydrofuran T=20°C; 5 h;

1: hydrogenchloride; palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 5 h / 20 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 °C 3: AlCl3, aluminium chloride / chloroform / 0.5 h / 0 °C 4: sodium tetrahydroborate; sodium hydroxide / water / 72 h / 20 °C 5: triethylsilane; trifluoroacetic acid / 16 h / 20 °C 6: AlCl3, aluminium chloride / toluene / 2 h / Reflux; Inert atmosphere View Scheme