N-ethyl-N,N-diisopropylamine in dichloromethane T=25°C; 2 h;

1.1: BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 84 percent / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.1: sec-BuLi; N,N,N',N'',N''-pentamethylethylenetriamine / tetrahydrofuran; cyclohexane / 2 h / -75 °C 2.2: 64 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; cyclohexane 3.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C 3.2: tetrahydrofuran; hexane 3.3: 65 percent / aq. HCl / pH 1 View Scheme