Reaktion #937105

Reaktionsgleichung

3-(2,4-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

compound 1-16

3-(2,4-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

potassium fluoride

butyl glycolate

water

→

3-[4-(butoxycarbonylmethoxy)-2-fluoro5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

Ausbeute 82.4%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturthe mixture was heated
3. 3
   Temperaturunder reflux for 1.5 hours
4. 4
   SonstigeAfter completion of the reaction
5. 5
   workup.WAITthe reaction mixture was left
6. 6
   Extraktionfollowed by extraction with ethyl acetate
7. 7
   WaschenThe organic layer was washed with saturated sodium chloride solution
8. 8
   Trocknendried with anhydrous magnesium sulfate
9. 9
   Einengenconcentrated

Vorschrift

Then, 7.61 g of 3-(2,4-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-16) was dissolved in 10 ml of 1,4-dioxane, to which 5.28 g of potassium fluoride and 9.0 g of butyl glycolate were added, and the mixture was heated under reflux for 1.5 hours. After completion of the reaction, the reaction mixture was left cooling to room temperature. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 8.37 g (yield, 82%) of 3-[4-(butoxycarbonylmethoxy)-2-fluoro5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (the present compound depicted below; m.p., 109.5° C.). ##STR40##

Quelle