potassium hydroxide in methanol; water 2 h; Heating;

N,N,N',N'',N''-pentamethyldiethylenetriamine; potassium tert-butylate; 2,2,6,6-tetramethylpiperidinyl-lithium in tetrahydrofuran; hexane T=-100°C;

1: 78 percent / butyllithium; 2,2,6,6-tetramethylpiperidine / hexane; tetrahydrofuran / -75 °C 2: 52 percent / butyllithium; 2,2,6,6-tetramethylpiperidine; N,N',N',N",N"-(pentamethyl)diethylenetriamine / potassium tert-butoxide / tetrahydrofuran; hexane / 2 h / -100 °C View Scheme

1: 78 percent / butyllithium; 2,2,6,6-tetramethylpiperidine / hexane; tetrahydrofuran / -75 °C 2: 52 percent / butyllithium; 2,2,6,6-tetramethylpiperidine; N,N',N',N",N"-(pentamethyl)diethylenetriamine / potassium tert-butoxide / tetrahydrofuran; hexane / 2 h / -100 °C View Scheme