potassium hydroxide; potassium permanganate in 1,4-dioxane 2 h; Yield given. Yields of byproduct given;

hydrogenchloride; sodium hydride 1) DMF, H2O, 60 deg C, 30 min; Yield given. Multistep reaction;

1: 92 percent / p-toluenesulphonic acid / ethanol 2: 1) n-BuLi / 1) hexane, ether, -30 to 0 deg C in 2 h, 2) ether, -50 deg C, 3 h 3: P2O5 / 60 °C View Scheme

1: oxoammonium salt; silica gel / dichloromethane / 24 h / 20 °C / |Acidic conditions 2: oxoammonium salt; 2,6-dimethylpyridine / dichloromethane / 20 °C / |Sealed tube View Scheme

1.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2.1: tetrahydrofuran / 0.17 h / 0 °C / |Inert atmosphere; |Sealed tube 2.2: 0 - 20 °C / |Inert atmosphere; |Sealed tube 2.3: 0 - 20 °C / |Inert atmosphere; |Sealed tube 3.1: oxoammonium salt; silica gel / dichloromethane / 24 h / 20 °C / |Acidic conditions 4.1: oxoammonium salt; 2,6-dimethylpyridine / dichloromethane / 20 °C / |Sealed tube View Scheme

1.1: tetrahydrofuran / 0.17 h / 0 °C / |Inert atmosphere; |Sealed tube 1.2: 0 - 20 °C / |Inert atmosphere; |Sealed tube 1.3: 0 - 20 °C / |Inert atmosphere; |Sealed tube 2.1: oxoammonium salt; silica gel / dichloromethane / 24 h / 20 °C / |Acidic conditions 3.1: oxoammonium salt; 2,6-dimethylpyridine / dichloromethane / 20 °C / |Sealed tube View Scheme

phosphorus pentoxide T=60°C;

n-butyllithium Yield given. Multistep reaction;

1: 1) n-BuLi / 1) hexane, ether, -30 to 0 deg C in 2 h, 2) ether, -50 deg C, 3 h 2: P2O5 / 60 °C View Scheme

sodium hydride 1) DMF, H2O, 60 deg C, 30 min, 2) DMF, 80 deg C, 30 min; Yield given. Multistep reaction;