lithium hydroxide hydrate in tetrahydrofuran; methanol; water T=20°C;

1: hydrogen; palladium 10 on activated carbon / ethanol / 12 h / 20 °C 2: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C 3: diethylamino-sulfur trifluoride / dichloromethane / 20 °C 4: potassium hydroxide / water; ethanol / 20 °C / |Cooling with ice 5: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / |Reflux 6: lithium hydroxide hydrate / water; tetrahydrofuran; methanol / 20 °C View Scheme

1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 20 °C 3: potassium hydroxide / water; ethanol / 20 °C / |Cooling with ice 4: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / |Reflux 5: lithium hydroxide hydrate / water; tetrahydrofuran; methanol / 20 °C View Scheme

1: potassium hydroxide / water; ethanol / 20 °C / |Cooling with ice 2: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / |Reflux 3: lithium hydroxide hydrate / water; tetrahydrofuran; methanol / 20 °C View Scheme

1: diphenyl phosphoryl azide; triethylamine / 1,4-dioxane / |Reflux 2: lithium hydroxide hydrate / water; tetrahydrofuran; methanol / 20 °C View Scheme