Réaction #43590

Équation de réaction

water

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

potassium carbonate

paraformaldehyde

→

product

Rendement 66.0%

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

Rendement 66.0%

Solvants

ethyl acetate

cyclohexane

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   AutreAfter separation
3. 3
   Extractionthe aqueous was re-extracted with ethyl acetate
4. 4
   Autrethe combined organic phases dried
5. 5
   Autreevaporated
6. 6
   LavageChromatography, eluting with 15% ethyl acetate/hexane

Mode opératoire

A mixture of methyl[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (35.79 g, 143 mmol), benzyltriethylammonium chloride (51.5 g), potassium carbonate (30.4 g) and paraformaldehyde (30.4 g) in cyclohexane (1 litre) was stirred at 80° C. under argon overnight, cooled and shaken with water and ethyl acetate. After separation, the aqueous was re-extracted with ethyl acetate and the combined organic phases dried and evaporated. Chromatography, eluting with 15% ethyl acetate/hexane, provided the product (24.66 g, 66%).

Source