1: 10N aq. NaOH / ethanol 3: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / Ambient temperature 4: 100 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 5: 91 percent / pyridine / 5 h 6: 1.) CuI / 1.) Et2O, -10 deg C, 30 min, 2.) Et2O, 0 deg C, 2 h 7: pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 8: pyridine / Ambient temperature 9: aq. NaIO4, RuCl3 / acetonitrile; CCl4 / 8 h / Ambient temperature 10: 10N aq. NaOH / ethanol / 0.5 h / Ambient temperature 12: 80 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme