Réaction #1853

Équation de réaction

2-bromo-3-benzyloxy-6-hydroxymethylpyridine

potassium acetate

n-butyl acrylate

→

n-Butyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoate

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
   AutreThis residue was purified by flash column chromatography
7. 7
   Lavageeluting with a gradient of ethyl acetate in dichloromethane
8. 8
   Autreto isolate the product

Mode opératoire

To a solution of 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10.0 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 25.0 mmol), tetra-n-butylammonium iodide (3.69 g, 10.0 mmol), bis(triphenylphosphine)palladium dichloride (281 mg, 0.4 mmol) and n-butyl acrylate (4.31 ml, 3.84 g, 30 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 3 h. The mixture was cooled and poured into 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. This residue was purified by flash column chromatography, eluting with a gradient of ethyl acetate in dichloromethane to isolate the product, an oil (2.72 g, 80%).

Source