تفاعل #172388

معادلة التفاعل

compound

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

tributylvinyltin

→

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

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is heated
2. 2
   درجة الحرارةat reflux for 16 h
3. 3
   درجة الحرارةto cool
4. 4
   ترشيحfiltered through kieselguhr
5. 5
   تركيزThe filtrates are concentrated to dryness under reduced pressure
6. 6
   أخرىThe residue is chromatographed on silica gel using a gradient of cyclohexane and ethyl acetate
7. 7
   تركيزconcentrated to dryness under reduced pressure
8. 8
   workup.ADDITIONPetroleum ether is added until crystallization sets in
9. 9
   ترشيحThe crystals are filtered off
10. 10
    أخرىdried under reduced pressure

الإجراء التجريبي

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.

المصدر