1: 82.8 percent / pyridinium tosylate / benzene / 14 h / Heating 2: 80 percent / NaI / acetone / 1 h / 50 °C View Scheme

pyridinium p-toluenesulfonate; sodium iodide 1.) benzene, reflux, 4 Angstroem mol. sieves, 2.) acetone; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 82.8 percent / pyridinium tosylate / benzene / 14 h / Heating 2: 80 percent / NaI / acetone / 1 h / 50 °C 3: 22 percent / Bu3SnH, AIBN / benzene / Heating 4: 85 percent / LiAlH4, AlCl3 / tetrahydrofuran / 1 h / -78 °C 5: 90 percent / methanol / 15 h / Ambient temperature 6: NaH / dioxane; dimethylformamide / 6 h / Heating View Scheme