Etherification;

1: triethylamine / acetonitrile / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 80 °C / |Reflux View Scheme

1: With diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in toluene Sonogashira-Hagihara coupling reaction; 2: With potassium hydroxide in tetrahydrofuran; methanol

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 12 h / 60 °C / |Schlenk technique 2: potassium hydroxide; water / tetrahydrofuran; methanol / 20 °C View Scheme