in acetonitrile 1.) 25 deg C, 1h, 2.) 55 deg C, 24h;

sulfuric acid T=60°C; 144 h; Inert atmosphere;

1: potassium carbonate; sodium iodide / dichloromethane / 16 h / |Reflux; |Inert atmosphere 2: thionyl chloride / dichloromethane / 2 h / 20 °C / |Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 16 h / 20 °C / |Inert atmosphere 4: sulfuric acid / 144 h / 60 °C / |Inert atmosphere View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=0 - 50°C; Inert atmosphere;

in diethyl ether

1: 1.) LDA / tetrahydrofuran / 0.58 h / -78 - 0 °C 2: O2, Rose Bengal / pentane; tetrahydrofuran / 0.08 h / 0 °C / photooxygenation View Scheme

1: With sodium hydroxide; ethanol; water T=20°C; 4 h; 2: With hydrogenchloride pH=7;