diisobutylaluminium hydride in diethyl ether; hexane T=-70 - 0°C;

1: 37 percent / KMnO4 / H2O 2: 85 percent / pyridine / 12 h 3: 91 percent / KOH / methanol / 48 h / Ambient temperature 4: 71 percent / PhCO3H / CHCl3 / 120 h / Ambient temperature 5: 1.) LiAlH4, 2.) pyridinium dichromate / 1.) Et2O, 2.) CH2Cl2, 2 h 6: 1.) NaH / 1.) Et2O, 2.) Et2O, 3 h, RT 7: POCl3, pyridine / diethyl ether / 72 h 8: 83 percent / 1 M (i-Bu)2AlH / diethyl ether; hexane / -70 - 0 °C View Scheme

1: 85 percent / pyridine / 12 h 2: 91 percent / KOH / methanol / 48 h / Ambient temperature 3: 71 percent / PhCO3H / CHCl3 / 120 h / Ambient temperature 4: 1.) LiAlH4, 2.) pyridinium dichromate / 1.) Et2O, 2.) CH2Cl2, 2 h 5: 1.) NaH / 1.) Et2O, 2.) Et2O, 3 h, RT 6: POCl3, pyridine / diethyl ether / 72 h 7: 83 percent / 1 M (i-Bu)2AlH / diethyl ether; hexane / -70 - 0 °C View Scheme

1: 1.) NaH / 1.) Et2O, 2.) Et2O, 3 h, RT 2: POCl3, pyridine / diethyl ether / 72 h 3: 83 percent / 1 M (i-Bu)2AlH / diethyl ether; hexane / -70 - 0 °C View Scheme