Ethyl Acrylate → 3-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl ester

Temperature

100 °C

To a solution of 2-chloro-5-iodopyridine(37.7 g) in DMF (300 mL) was added palladium(II) acetate (1.77 g), tri-o-tolylphosphine (7.19 g), diisopropylethylamine (82 mL), and ethyl acrylate (17.9 mL), and the mixture was heated at 100° C. for 10 hours. Resulting mixture was poured into water and extracted with AcOEt. The organic layer was washed with water and brine and dried over Na2SO4, and the solvent was removed in vacuo. Obtained brown solid was suspended in a mixture of hexane and AcOEt(4:1), and the precipitate was filtered off. The filtrate was concentrated in vacuo, and residual brown oil was purified by silica gel column chromatography eluted with AcOEt and hexane (1:4-1:2). Resulting solid was triturated with IPE to give ethyl (2E)-3-(6-chloro-3-pyridyl)acrylate as pale yellow powder (20.58 g).

1. customResulting mixture
2. extractionextracted with AcOEt
3. washThe organic layer was washed with water and brine
4. dry with materialdried over Na2SO4
5. customthe solvent was removed in vacuo
6. customObtained brown solid
7. filtrationthe precipitate was filtered off
8. concentrationThe filtrate was concentrated in vacuo, and residual brown oil
9. customwas purified by silica gel column chromatography
10. washeluted with AcOEt and hexane (1:4-1:2)
11. customResulting solid
12. customwas triturated with IPE

ORD record

ord-8a331c607eb04efb98093746d0496732

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557127B2