1: With tert.-butyl lithium in tetrahydrofuran T=-100°C; 1 h; 2: With hydrogenchloride in tetrahydrofuran 0.166667 h;

1.1: 73 percent / NaNO2; TMS-Br; PhCH2NEt3Br / dimethylformamide / 2 h / 0 °C 2.1: 86 percent / CDI; DMAP / dimethylformamide / 20 °C 3.1: t-BuLi / tetrahydrofuran / 1 h / -100 °C 3.2: 42 percent / aq. HCl / tetrahydrofuran / 0.17 h View Scheme

1.1: 86 percent / CDI; DMAP / dimethylformamide / 20 °C 2.1: t-BuLi / tetrahydrofuran / 1 h / -100 °C 2.2: 42 percent / aq. HCl / tetrahydrofuran / 0.17 h View Scheme

sodium hydroxide 2 h; Heating;