Methyl Acrylate → methyl (E)-3-(3-quinolinyl)-2-propenoate

Temperature

100 °C

A Fisher-Porter pressure bottle was charged with 3-bromoquinoline (2.77 mL, 20 mmol), methyl acrylate (2.25 mL, 25 mmol), palladium diacetate (44 mg, 0.2 mmol), and tri-o-tolylphosphine (244 mg, 0.802 mmol) in Et3N (10 mL). The atmosphere was replaced with argon, the bottle sealed and the mixture was stirred and heated at 100° C. for 6 h. The cooled mixture was partitioned between CH2Cl2 (200 mL) and H2O (100 mL) and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with H2O (100 mL) dried (Na2SO4) and concentrated to give 5.56 g of crude product which was purified by silica gel chromatography, eluting with a mixture of EtOAc and hexane in (1:1) to give (E)-3-(3-quinolinyl)-2-propenoic acid methyl ester (4.26 g, 20 mmol) in quantitative yield, mp 118° -120° C.

1. customthe bottle sealed
2. customThe cooled mixture was partitioned between CH2Cl2 (200 mL) and H2O (100 mL)
3. extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
4. washThe combined organic layers were washed with H2O (100 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customto give 5.56 g of crude product which
8. customwas purified by silica gel chromatography
9. washeluting with a mixture of EtOAc and hexane in (1:1)

ORD record

ord-fc8c5400766344f8b327adf56fe50d56

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05128448