2,4,6-trimethyl-pyridine; lithium iodide T=180°C; 16 h;

1: 89 percent / PBr3 / 12 h 2: dimethylsulfoxide / 3.5 h 3: 52 percent / dimethylsulfoxide / 6.5 h / 120 - 130 °C 4: 89 percent / LiI, 2,4,6-collidine / 16 h / 180 °C View Scheme

1: 52 percent / dimethylsulfoxide / 6.5 h / 120 - 130 °C 2: 89 percent / LiI, 2,4,6-collidine / 16 h / 180 °C View Scheme

1: 89 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 89 percent / PBr3 / 12 h 3: dimethylsulfoxide / 3.5 h 4: 52 percent / dimethylsulfoxide / 6.5 h / 120 - 130 °C 5: 89 percent / LiI, 2,4,6-collidine / 16 h / 180 °C View Scheme