Methyl Acrylate → 3-Pyridineacrylic acid, methyl ester

HRID 22486Notes

Reaction equation

HRID 22486 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2](/[CH:10]=[CH:9]/[C:8]([O:12][CH3:13])=[O:11])[CH:3]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 122863-BromopyridineHCID 80271Tri-o-tolylphosphine

Product 1

HCID 53576873-Pyridineacrylic acid, methyl esterYield 12.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromopyridine (4 g, 25 mmol), methyl acrylate (2.6 g, 31 mmol), palladium(II) acetate (0.26 g, 1.2 mmol), tri-o-tolylphosphine (0.74 g, 2.4 mmol) and triethylamine (10 ml) were placed in a thick walled glass tube. The tube was sealed under argon and the mixture heated at 80° C. After 12 h the reaction mixture was allowed to cool to room temperature and chloroform (100 ml) was added. The mixture was washed with water (2×100 ml), the organics dried over anhydrous magnesium sulphate, and the solvent removed under reduced pressure. Column chromatography (flash silica gel; 1:1 ethyl acetate/hexane) yielded methyl E-3-(3-pyridyl)acrylate as a colourless oil (0.5 g, 12%).

Workup

  1. customThe tube was sealed under argon
  2. temperatureto cool to room temperature
  3. washThe mixture was washed with water (2×100 ml)
  4. dry with materialthe organics dried over anhydrous magnesium sulphate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-eb127e8b7fa24affb4f5a433c52fa56f
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Reaction notes

Loading…