Diethyl Carbonate → 6-Fluoro-4-hydroxycoumarin

HRID 2190919노트

반응식

HRID 2190919 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:12]([O:14]C(=O)OCC)C.CC(C)([O-])C.[K+]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:12](=[O:14])[CH:9]=[C:8]2[OH:10]

참가 물질

5

반응물 3

HCID 7766Diethyl CarbonateHCID 959922-Acetyl-4-fluorophenolHCID 23665647Potassium tert-butoxide

생성물 1

HCID 546914066-Fluoro-4-hydroxycoumarin수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-(5-Fluoro-2-hydroxy-phenyl)-ethanone (1.54 g, 10 mmol) and diethylcarbonate (2.42 mL, 20 mmol) were placed in a dry flask and dissolved in anhydrous tetrahydrofuran (30 mL.) The solution was then added drop-wise via cannula to a rapidly stirring solution of potassium tert-butoxide in tetrahydrofuran (1.0 M, 30 mL) The reaction was permitted to stir overnight (10 h) at room temperature under positive pressure of nitrogen. The crude reaction was concentrated under reduced pressure and partitioned between methyl tert-butyl ether and water. The layers were separated and the organic phase discarded. The aqueous phase was acidified to pH 5 and extracted three times with equal volumes of methylene chloride. The combined organic phases were dried over sodium sulfate and concentrated to give the title compound (1.4 g, 78% yield.) MS ESI(−) m/e: 179.16 (M−1).

후처리

  1. customThe crude reaction
  2. concentrationwas concentrated under reduced pressure
  3. custompartitioned between methyl tert-butyl ether and water
  4. customThe layers were separated
  5. extractionextracted three times with equal volumes of methylene chloride
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f0fb5395ed3e4826ba67a0b53292924e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324405B2

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