1: 1-n-pentyne With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.333333 h; Inert atmosphere; 2: zinc(II) chloride in tetrahydrofuran; hexane T=-78°C; 0.5 h; Inert atmosphere;

1.1: 65 percent / Pd(dba)2; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 5 h / 65 °C 2.1: LiOH / H2O; methanol / 18 h / 5 °C 2.2: 94 percent / H2SO4 / H2O / 0 °C View Scheme

diisobutylaluminium hydride; Ni(PPh3)4 in tetrahydrofuran; hexane 2 h; Ambient temperature;