pyridinium chlorochromate in dichloromethane 0.5 h; Ambient temperature;

pyridinium p-toluenesulfonate in ethanol T=55°C; 4 h;

lithium n-butyldiisobutylaluminum hydride in toluene

1: 1.) Mg / 1.) ether; 2.) ether, 0.5 h 2: 18 percent / phosphorus oxychloride, pyridine / 2.33 h View Scheme

1: 96 percent / pyridine / 1.) 0 deg C, 30 min, 2.) RT, 20 h 2: 4 percent / pyridinium p-toluenesulfonate (PPTS) / ethanol / 4 h / 55 °C View Scheme

1: 94 percent / lithium aluminum hydride / diethyl ether / 1.) from -77 deg C to -60 deg C, 2.) -45 deg C, 15 min 2: 96 percent / pyridine / 1.) 0 deg C, 30 min, 2.) RT, 20 h 3: 4 percent / pyridinium p-toluenesulfonate (PPTS) / ethanol / 4 h / 55 °C View Scheme