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

HRID 83423ノート

反応式

HRID 83423 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-e47c3e76e32146b4a71b5e5803b28d98
出典データセット
uspto-grants-2014_09
特許番号
US08846719B2

反応ノート

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