Reaktion #43580

Reaktionsgleichung

ethyl acetate

paraformaldehyde

methyl[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate

potassium carbonate

→

desired compound

Ausbeute 89.0%

Methyl 2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoate

Ausbeute 89.0%

Lösungsmittel

water

cyclohexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   SonstigeAfter separation
3. 3
   Extraktionthe aqueous was extracted with ethyl acetate
4. 4
   SonstigeThe combined organic phases were dried
5. 5
   Sonstigethe solvent was removed

Vorschrift

A mixture of methyl[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43.3 g, 162 mmol), benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g) in cyclohexane (1060 ml) was heated at 80° C. for 24 h, cooled and treated with ethyl acetate and water. After separation, the aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using hexane/15% ethyl acetate to provide the desired compound (40.2 g, 89%).

Quelle