1: With ozone in methanol; dichloromethane T=-78°C; 0.166667 h; 2: With sodium tetrahydroborate in methanol; dichloromethane T=-78 - 20°C; 16 h; 3: With water; ammonium chloride in methanol; dichloromethane

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Reflux 1.2: 0 °C 1.3: 12 h / 20 °C 2.1: ozone / dichloromethane; methanol / -78 °C / Inert atmosphere 2.2: 16 h / -78 °C 2.3: 1 h / -78 - 20 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Reflux 1.2: 0 °C 1.3: 12 h / 20 °C 2.1: ozone / dichloromethane; methanol / -78 °C / Inert atmosphere 2.2: 16 h / -78 °C 2.3: 1 h / -78 - 20 °C View Scheme

1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 2: ammonium hydroxide / copper(l) iodide / water / 16 h / 100 °C / sealed tube View Scheme