pyridine; 4-(N,N-dimethlyamino)pyridine T=0°C;

1: 95 percent / (4-dimethylamino)pyridine (DMAP), pyridine / 0 °C 2: 1.) Cu2I2 / 1.) Et2O, 0 deg C, 30 min, 2.) Et2O, RT, 48 h 3: 100 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 4: 100 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / Ambient temperature 5: 1.) n-BuLi / 1.) hexane, THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 90 min 6: 76 percent / AG-50WX4(resin) / methanol / 16 h / Ambient temperature View Scheme