potassium carbonate in acetone 6 h; Inert atmosphereReflux;

anhydrous sodium benzoate T=180 - 190°C; P=12 Torr; 3 h;

1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 60 °C / Inert atmosphere 2.1: sodium tetrahydroborate / ethanol / 20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.2: Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Reflux 4.1: potassium carbonate / acetone / 6 h / Inert atmosphere; Reflux View Scheme

1.1: sodium tetrahydroborate / ethanol / 20 °C / Inert atmosphere; Cooling with acetone-dry ice 1.2: Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Reflux 3.1: potassium carbonate / acetone / 6 h / Inert atmosphere; Reflux View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 60 °C / Inert atmosphere 2.1: sodium tetrahydroborate / ethanol / 20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.2: Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Reflux 4.1: potassium carbonate / acetone / 6 h / Inert atmosphere; Reflux View Scheme

1.1: titanium tetrachloride / dichloromethane / -20 - 0 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 60 °C / Inert atmosphere 3.1: sodium tetrahydroborate / ethanol / 20 °C / Inert atmosphere; Cooling with acetone-dry ice 3.2: Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Reflux 5.1: potassium carbonate / acetone / 6 h / Inert atmosphere; Reflux View Scheme

in methanol 48 h; Ambient temperature;

1: ethanol; pentyl nitrite; aqueous hydrochloric acid 2: acetone View Scheme

1: sodium benzoate / 190 °C / unter vermindertem Druck; Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge 2: acetone; potassium carbonate View Scheme

1: sodium benzoate / 190 °C / unter vermindertem Druck; Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge 2: acetone; potassium carbonate View Scheme