pyridinium p-toluenesulfonate in methanol T=55°C; 18 h; Yield given;

1: pyridinium toluene-p-sulphonate / methanol / 18 h / 55 °C 2: 89 percent / H2 / palladized barium sulphate (5percent) / pyridine / 2 h 3: 82 percent / pyridine / CHCl3 / 6 h / 0 °C 4: 100 percent / sodium iodide / acetone / 48 h / Ambient temperature 5: 93 percent / acetonitrile / 48 h / 80 °C 6: 1) butyl-lithium, 2) hexamethylphosphoric triamide / hexane, THF, 1) - 78 deg C, 0.5 h, 2) - 78 deg C, 2 h 7: 100 percent / LiAlH4 / tetrahydrofuran / 0.25 h 8: 100 percent / 1percent aq. iron(III)chloride / benzene / 0.25 h View Scheme

1: pyridinium toluene-p-sulphonate / methanol / 18 h / 55 °C 2: 89 percent / H2 / palladized barium sulphate (5percent) / pyridine / 2 h View Scheme