Potassium Carbonate → HCID 86679287, compound

Participants

Reaction Steps

4-Methoxycarbonylphenylboronic acid (1.0 g), PdCl2(PPh3)2 (0.18 g), triphenylphosphine (0.13 g) and potassium carbonate (1.4 g) were added to a toluene (5.0 mL)-ethanol (2.5 mL) solution of 4-((E)-4-chlorobut-3-en-1-yn-1-yl)benzaldehyde (0.97 g) as obtained in Example 22-(1), and the mixture was heated and refluxed for 3 hours in a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, ethyl acetate was added, the insolubles were filtered out, and the filtrate was concentrated under reduced pressure. IPE was added to the resulting residue, and the solids were filtered out, whereafter chloroform and OH type silica gel (10 g) were added. The insolubles were filtered out, and the filtrate was concentrated under reduced pressure to obtain 4-[(1E)-4-(4-formylphenyl)but-1-en-3-yn-1-yl]benzoic acid methyl ester (light brown solid) (1.2 g, 78%).

Provenance & Evidence