2,6-dimethylpyridine; lithium iodide 3 h; Heating; Yield given;

1: triethylamine / 16 h / 0 - 25 °C / |Inert atmosphere 2: neat (no solvent) / 160 °C / |Inert atmosphere 3: anhydrous potassium trimethylsilanolate / tetrahydrofuran / 2 h / 70 °C / |Inert atmosphere View Scheme

1: thionyl chloride / 78 °C / |Inert atmosphere 2: triethylamine / 16 h / 0 - 25 °C / |Inert atmosphere 3: neat (no solvent) / 160 °C / |Inert atmosphere 4: anhydrous potassium trimethylsilanolate / tetrahydrofuran / 2 h / 70 °C / |Inert atmosphere View Scheme

1: 59 percent / 0.08 h / 170 °C 2: 1.) n-butyllithium / 1.) THF, hexane, RT, 2 h, 2.) Et2O View Scheme

1: 59 percent / 0.08 h / 170 °C 2: 1.) n-butyllithium / 1.) THF, hexane, RT, 2 h, 2.) Et2O View Scheme

n-butyllithium 1.) THF, hexane, RT, 2 h, 2.) Et2O; Yield given. Multistep reaction;

1: 1.) triethylamine, ethyl chloroformate, 2.) tetramethylguanidinium azide / 1.) THF, 0 deg C, 1 h, 2.) chloroform, 0 deg C, 2.5 h 2: 90 percent / benzene / Heating View Scheme