hydrogenchloride; magnesium in tetrahydrofuran; ethyl acetate

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.0833333 h; Inert atmosphere; 2: With boric acid trimethyl ester in tetrahydrofuran; diethyl ether; hexane T=-50°C; 0.5 h; Inert atmosphere; 3: With hydrogenchloride in tetrahydrofuran; diethyl ether; hexane; water T=20°C;

1.1: potassium carbonate / acetone / 16 h / Inert atmosphere; Reflux 2.1: acetone / 16 h / Inert atmosphere; Reflux 3.1: sodium hydroxide / methanol / 12 h / Inert atmosphere; Reflux 3.2: pH 1 4.1: potassium carbonate / ethanol / 16 h / Inert atmosphere; Reflux 5.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere 5.2: 0.5 h / -50 °C / Inert atmosphere 5.3: 20 °C View Scheme

1.1: acetone / 16 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / methanol / 12 h / Inert atmosphere; Reflux 2.2: pH 1 3.1: potassium carbonate / ethanol / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -50 °C / Inert atmosphere 4.3: 20 °C View Scheme