diethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide T=45°C; Sonogashira coupling;

1: 3-(2,4,6-trimethylphenyl)prop-2-yn-1-ol With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.25 h; 2: monobromoacetic acid With n-butyllithium in tetrahydrofuran; hexane T=20°C; 24 h;

1.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 1.2: 44 percent / BuLi / hexane; tetrahydrofuran / 24 h / 20 °C 2.1: 181 mg / [2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium]*BF4; (i-Pr)2NEt / CH2Cl2 / 15 h 3.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 3.2: 37 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme