Réaction #1854

Équation de réaction

2-bromo-3-benzyloxy-6-hydroxymethylpyridine

potassium acetate

methyl acrylate

→

product

Rendement 84.1%

Methyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoate

Rendement 84.1%

Solvants

water

DMF

water

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled
2. 2
   ExtractionThe product was extracted into ethyl acetate (3×30 ml)
3. 3
   LavageThe combined extracts were washed with water (3×25 ml)
4. 4
   Autredried
5. 5
   Autreevaporated
6. 6
   AutreThe residue was purified by flash column chromatography
7. 7
   Lavageeluting with dichloromethane

Mode opératoire

To a solution of 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 10.0 mmol), tetra-n-butylammonium iodide (3.69 g. 10.0 mmol), bis(triphenyl-phosphine)palladium dichloride (281 mg, 0.4 mmol) and methyl acrylate (2.70 ml. 2.58 g, 30 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 5 h. The mixture was cooled and added to water (180 ml). The product was extracted into ethyl acetate (3×30 ml). The combined extracts were washed with water (3×25 ml), dried and evaporated. The residue was purified by flash column chromatography eluting with dichloromethane, then 4:1 dichloromethane:ethyl acetate to give the product (2.516 g, 84%).

Source