Water → HCID 178468879, Verbindung

HRID 70531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70531
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[Cl:14][C:15]1[CH:20]=[N+:19]([O-])[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1.O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:19][C:20]=1[OH:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 67397297Ethyl 5-chloropyridine-2-carboxylate 1-oxide

Produkt 1

HCID 178468879HCID 178468879, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Trifluoroacetic anhydride (147 mL) was added dropwise to a solution of ethyl 5-chloropyridine-2-carboxylate 1-oxide (36.8 g) in N,N-dimethylformamide (220 mL) under ice-cooling over 20 minutes, and the mixture was stirred at 50° C. for one hour. The reaction solution was ice-cooled and water was added. Sodium bicarbonate was slowly added to effect neutralization, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was suspended with ethyl acetate, stirred and then filtered. The filtrate was concentrated under reduced pressure. The same operation was further repeated twice. The resulting solids were combined and dried under reduced pressure to give ethyl 5-chloro-6-hydroxypyridine-2-carboxylate as a white solid (24.2 g, 75%). The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give ethyl 5-chloro-6-hydroxypyridine-2-carboxylate as a white solid (1.84 g, 6%).

Aufarbeitung

  1. temperaturecooling over 20 minutes
  2. temperaturecooled
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. stirringstirred
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35ecbc7327cc4c0dbebe58e1a13ce403
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

Notizen zur Reaktion

Wird geladen…