copper(II) oxide; copper dichloride in water; acetone

1: para-bromobenzonitrile; 3-hydroxy-3-phenyl-prop-1-yne With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Sonogashira coupling; 16 h; Heating; 2: benzaldehyde With N-methyl-4-methyl-5-(2-hydroxyethyl)thiazolin iodide in triethylamine Stetter reaction; 8 h; Heating; Further stages.;

1: Et3N; CuI / (Ph3P)2PdCl2 / 14 h / Heating 2: 285 mg / Et3N; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide / tetrahydrofuran / 24 h / Heating View Scheme

1: 1.) n-butyllithium, 2.) cuprous iodide / THF, -75 gradC 2: 84 percent / cupric chloride, cupric oxide / acetone; H2O View Scheme

1: 1.) n-butyllithium, 2.) cuprous iodide / THF, -75 gradC 2: 84 percent / cupric chloride, cupric oxide / acetone; H2O View Scheme

3,4-dimethyl-5-(2-hydroxyethyl)-thiazolium iodide; triethylamine in tetrahydrofuran Stetter reaction; 24 h; Heating;

ammonium acetate in acetic acid T=130°C; 3 h;