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

Temperatur

120 °C

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%).

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. customThe residue was purified by flash column chromatography
7. washeluting with dichloromethane

ORD-Eintrag

ord-a748f251ca1d423aa7e17eaf3d09ac7f

Quelldatensatz

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05726315