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

HRID 332026노트

반응식

HRID 332026 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 234478853-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acid수율 94.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-1a9d42c01289436b819de164bd8a20cb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877782B2

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