1: (E)-1-chloro-6-phenyl-1-hexene-3,5-diyne With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: methyl iodide in tetrahydrofuran; hexane T=-78 - 20°C;

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 74 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 6 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme