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

HRID 1531432노트

반응식

HRID 1531432 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cda3ac20f3a54a9a94e07f52f709dd8a
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06197978B1

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