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

Temperatur

120 °C

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%).

1. temperatureThe mixture was cooled
2. extractionThe product was extracted into ethyl acetate (3×30 ml)
3. washThe combined extracts were washed with water (3×25 ml)
4. customdried
5. customevaporated
6. customThis residue was purified by flash column chromatography
7. washeluting with a gradient of ethyl acetate in dichloromethane
8. customto isolate the product

ORD-Eintrag

ord-cbc402db79bd4ddea3a7284194868b01

Quelldatensatz

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05726315