Reaction #172388

Reaction equation

compound

3-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

tributylvinyltin

→

1-(2-Methoxy-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

Solvents

dioxane

Conditions

Workup

1. 1
   TemperatureThe mixture is heated
2. 2
   Temperatureat reflux for 16 h
3. 3
   Temperatureto cool
4. 4
   Filtrationfiltered through kieselguhr
5. 5
   ConcentrationThe filtrates are concentrated to dryness under reduced pressure
6. 6
   OtherThe residue is chromatographed on silica gel using a gradient of cyclohexane and ethyl acetate
7. 7
   Concentrationconcentrated to dryness under reduced pressure
8. 8
   workup.ADDITIONPetroleum ether is added until crystallization sets in
9. 9
   FiltrationThe crystals are filtered off
10. 10
    Otherdried under reduced pressure

Procedure

100 g (308 mmol) of the compound from Example 19A are dissolved in 1.4 l of anhydrous dioxane, and 8.9 g (7.7 mmol) of tetrakis(triphenylphospine)palladium and 117 g (370 mmol) of tributylvinyltin are added. The mixture is heated at reflux for 16 h. The reaction solution is then allowed to cool and filtered through kieselguhr. The filtrates are concentrated to dryness under reduced pressure. The residue is chromatographed on silica gel using a gradient of cyclohexane and ethyl acetate. The product-containing fractions are combined and concentrated to dryness under reduced pressure. Petroleum ether is added until crystallization sets in. The crystals are filtered off and dried under reduced pressure. This gives 37 g (41% of theory) of the desired product.

Source