Sodium Hydroxide → 8-fluoro-2H-chromene-5-carboxylic acid

HRID 1531432ノート

反応式

HRID 1531432 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]([O:14]C)=[O:13])=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]=[CH:7]2.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]([OH:14])=[O:13])=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]=[CH:7]2

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 12016893Methyl 8-fluoro-2H-1-benzopyran-5-carboxylate

生成物 1

HCID 120168948-fluoro-2H-chromene-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Methyl 8-fluoro-2H-1-benzopyran-5-carboxylate (7.36 g, 35.4 mmol) was dissolved in absolute ethanol (220 mL), NaOH (2.0 g, 49.6 mmol) in H2O (25 mL), was added thereto, and the reaction mixture was refluxed for 1.5 hour. The reaction mixture was cooled and the solvent was removed in vacuo. The yellow solid was dissolved in H2O (150 mL), active charcoal was added and then filtered off. The resulting light-coloured liquid was washed with diethyl ether, the aqueous solution was made acidic with 2 M HCl and the product was extracted twice with ethyl acetate. The combined organic portions were treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give 6.64 g (97% yield) of a yellowish solid (dried in a desiccator over P2O5) as the title compound (mp 224-226° C.). EIMS (70 eV) m/z (relative intensity) 194 (93, M+), 193 (100), 149 (56), 148 (68), 120 (13), 88 (25), 75 (28), 74 (21), 60 (12).

後処理

  1. temperaturethe reaction mixture was refluxed for 1.5 hour
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed in vacuo
  4. dissolutionThe yellow solid was dissolved in H2O (150 mL)
  5. additionactive charcoal was added
  6. filtrationfiltered off
  7. washThe resulting light-coloured liquid was washed with diethyl ether
  8. extractionthe product was extracted twice with ethyl acetate
  9. additionThe combined organic portions were treated with brine
  10. dry with materialdried with MgSO4
  11. filtrationfiltered
  12. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-cda3ac20f3a54a9a94e07f52f709dd8a
出典データセット
uspto-grants-2001_03
特許番号
US06197978B1

反応ノート

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