Réaction #50764

Équation de réaction

3-Bromopyridine

methyl acrylate

tri-o-tolylphosphine

triethylamine

→

methyl E-3-(3-pyridyl)acrylate

Rendement 12.3%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   AutreThe tube was sealed under argon
2. 2
   Températureto cool to room temperature
3. 3
   LavageThe mixture was washed with water (2×100 ml)
4. 4
   Séchagethe organics dried over anhydrous magnesium sulphate
5. 5
   Autrethe solvent removed under reduced pressure

Mode opératoire

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%).

Source