1.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -20 °C 1.2: 71 percent / tetrahydrofuran / 12 h / 20 °C 2.1: 73 percent / H2; quinoline / Pd-BaSO4 / hexane / 2 h / 20 °C / 760 Torr View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -20 °C 1.2: 71 percent / tetrahydrofuran / 12 h / 20 °C 2.1: 73 percent / H2; quinoline / Pd-BaSO4 / hexane / 2 h / 20 °C / 760 Torr View Scheme

1: CTPB With n-butyllithium in tetrahydrofuran; dimethyl sulfoxide T=10 - 15°C; 0.0833333 h; 2: pelargonaldehyde in tetrahydrofuran; dimethyl sulfoxide T=20°C; 0.5 h;

1.1: 5 h / 140 °C / N2 atmosphere 2.1: n-BuLi in hexane / tetrahydrofuran; dimethylsulfoxide / 0.08 h / 10 - 15 °C 2.2: tetrahydrofuran; dimethylsulfoxide / 0.5 h / 20 °C View Scheme