反应详情

4-Formylphenylboronic acid (0.49 g), PdCl2(PPh3)2 (0.11 g), triphenylphosphine (78 mg) and potassium carbonate (0.82 g) were added to a toluene (3.5 mL)-ethanol (1.8 mL) solution of 4-((E)-4-chlorobut-3-en-1-yn-1-yl)benzoic acid methyl ester (0.70 g) as obtained by the method described in the patent (WO2008/154642), 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 and IPA were 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-[(E)-4-(4-formylphenyl)but-3-en-1-yn-1-yl)benzoic acid methyl ester (orange solid) (0.59 g, 69%).

1. customas obtained by the method
2. temperaturethe mixture was heated
3. temperaturerefluxed for 3 hours in a nitrogen atmosphere
4. filtrationthe insolubles were filtered out
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionIPE and IPA were added to the resulting residue
7. filtrationthe solids were filtered out, whereafter chloroform and OH type silica gel (10 g)
8. additionwere added
9. filtrationThe insolubles were filtered out
10. concentrationthe filtrate was concentrated under reduced pressure