T=150°C; P=15 Torr; 1.5 h;

1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature View Scheme

1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 3: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating View Scheme

1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 3: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating 4: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min 5: 1) ozone, 2) pyridine / 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp. View Scheme