Water → (5-Fluoro-3-nitro-pyridin-2-yloxy)-acetic acid methyl ester

HRID 1943755

Reaktionsgleichung

Reaktionsgleichung von HRID 1943755
[CH3:1][O:2][C:3](=[O:6])[CH2:4][OH:5].[H-].[Na+].Cl[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([F:19])=[CH:12][N:11]=1.O>O1CCCC1>[CH3:1][O:2][C:3](=[O:6])[CH2:4][O:5][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([F:19])=[CH:12][N:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 107736262-Chloro-5-fluoro-3-nitropyridine

Produkt 1

HCID 66936775(5-Fluoro-3-nitro-pyridin-2-yloxy)-acetic acid methyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Hydroxy-acetic acid methyl ester (0.96 g, 10.7 mmol) was dissolved in 2 ml of anhydrous tetrahydrofuran under nitrogen atmosphere, and sodium hydride (0.42 g, 10.7 mmol) was added thereto at room temperature. After stirring for 30 minutes, 2-chloro-5-fluoro-3-nitro-pyridine (1.57 g, 8.89 mmol) dissolved in 15 ml of anhydrous tetrahydrofuran was added dropwise at room temperature, and the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction by adding water, the mixture was extracted with dichloromethane, and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of n-hexane:ethyl acetate=9:1. The fractions containing the product were collected and evaporated to obtain (5-fluoro-3-nitro-pyridin-2-yloxy)-acetic acid methyl ester as yellow liquid (1.35 g, 66%).

Aufarbeitung

  1. customat room temperature
  2. additionwas added dropwise at room temperature
  3. stirringthe reaction mixture was stirred at room temperature for 18 hours
  4. customAfter completion of the reaction
  5. extractionthe mixture was extracted with dichloromethane
  6. washthe combined organic layer was washed with water and saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica eluting with a solvent of n-hexane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-694f18d219f149b28f16a88449444eca
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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