1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran T=-78°C; 0.75 h; 2: With tert.-butyl lithium in tetrahydrofuran; pentane T=-78 - 20°C;

1.1: sec-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 70 percent / tetrahydrofuran; cyclohexane / -78 - 20 °C 2.1: 81 percent / LDA / tetrahydrofuran / -78 - 20 °C 3.1: 85 percent / NaBH4; NaOH / methanol; H2O / 13 h / Heating View Scheme

1: 1.) N,N,N',N'-tetramethylethylenediamine, s-BuLi / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h 2: 99 percent / p-toluenesulfonic acid / toluene / 2 h / Heating 3: 93 percent / hydrogen / Pd/C / ethyl acetate / 48 h View Scheme

1.1: tert-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 100 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 85 percent / acetic acid; hydrochloric acid / 22 h / Heating View Scheme

1.1: sec.-butyllithium; N,N,N',N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / |Inert atmosphere 1.2: -78 - 20 °C / |Inert atmosphere 2.1: hydrogenchloride; acetic acid; water / 12 h / |Reflux View Scheme