1: 1.) n-C4H9Li / 1.) THF, -110 deg C; 2.) room temp., 1.5 h 2: tetrahydrofuran; toluene / Heating View Scheme

1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-70°C; 0.583333 h; Inert atmosphere; 2: With hydrogenchloride in tetrahydrofuran; hexane; water Cooling with iceInert atmosphere; Mechanism; Reagent/catalyst;

potassium hydroxide in dimethyl sulfoxide T=20°C; 102 h; Mechanism;

sodium tetrahydroborate in diethylene glycol dimethyl ether T=150°C; 3.5 h;

1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-70°C; 2: With hydrogenchloride in tetrahydrofuran; hexane; water T=20°C;

potassium hydroxide in dimethyl sulfoxide T=20°C; 102 h; Mechanism;