1: phenylacetylene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.25 h; 2: N-methyl-N-methoxy-2-{[3-(4-methylphenyl)prop-2-yn-1-yl]oxy}acetamide in tetrahydrofuran; hexane T=-78 - 20°C;

1.1: 67 percent / (i-Pr)2NH / PdCl2(PPh3)2; CuI / tetrahydrofuran 2.1: aq. KOH / methanol / 12 h 3.1: 0.96 g / [2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium]*BF4; (i-Pr)2NEt / CH2Cl2 / 12 h 4.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 4.2: 67 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme

1.1: 67 percent / (i-Pr)2NH / PdCl2(PPh3)2; CuI / tetrahydrofuran 2.1: aq. KOH / methanol / 12 h 3.1: 0.96 g / [2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium]*BF4; (i-Pr)2NEt / CH2Cl2 / 12 h 4.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 4.2: 67 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme

1.1: aq. KOH / methanol / 12 h 2.1: 0.96 g / [2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium]*BF4; (i-Pr)2NEt / CH2Cl2 / 12 h 3.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 3.2: 67 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme