Hydrochloric Acid → 3-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acid

HRID 332026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332026
C([O:3][C:4]([C:6]1[C:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:8][O:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=2)=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 743179Ethyl 3-(4-fluorophenyl)-1,2-oxazole-4-carboxylate

Produkt 1

HCID 234478853-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acidAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3-(4-fluoro-phenyl)-isoxazole-4-carboxylic acid ethyl ester (849 g, 208 mmol) in ethanol (215 mL) was added aqueous sodium hydroxide (2 N, 161 mL, 323 mmol) and the resulting mixture stirred overnight at room temperature. The mixture was then acidified with HCl solution (4 N, 85 mL) to pH 2-3. The precipitate was then filtered off and dissolved in THF (700 mL) and then washed with saturated sodium chloride solution. The aqueous phase was then extracted with ethyl acetate and THF (1:1, 300 mL) and the combined organic phases dried over sodium sulfate and evaporated to afford the title compound (40.8 g, 94%) which was obtained as an orange solid. MS: m/e=206.1 [M−H]−.

Aufarbeitung

  1. filtrationThe precipitate was then filtered off
  2. dissolutiondissolved in THF (700 mL)
  3. washwashed with saturated sodium chloride solution
  4. extractionThe aqueous phase was then extracted with ethyl acetate and THF (1:1, 300 mL)
  5. dry with materialthe combined organic phases dried over sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1a9d42c01289436b819de164bd8a20cb
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877782B2

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