oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-60°C; 0.25 h;

hydrogen; triphenylphosphine; [Rh(μ-OAc)(COD)]2 in benzene T=90°C; P=15001.2 Torr;

1: 1.) n-BuLi / 1.) THF, hexane, -20 deg C, 1.5 h, 2.) a) -78 deg C, 2 h, b) -78 deg C to 0 deg C, 3 h 2: 100 percent / H2 / 10percent Pd/C / petroleum ether / 12 h / 11250.9 Torr 3: 90 percent / LiAlH4 4: 67 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C View Scheme

1: 100 percent / H2 / 10percent Pd/C / petroleum ether / 12 h / 11250.9 Torr 2: 90 percent / LiAlH4 3: 67 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C View Scheme

1: 90 percent / LiAlH4 2: 67 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 0.25 h / -60 °C View Scheme