Furo[3,4-b]pyridine-5,7-dione → 2-(2-Benzyloxy-4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid

HRID 861326

Reaktionsgleichung

Reaktionsgleichung von HRID 861326
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]([O:9][C:10](=[O:11])[C:2]=12)=[O:8].[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[Li])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OC1C=C(OC)C=CC=1Br)C1C=CC=CC=1.[Li]CCCC>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:10]([C:2]1[C:3]([C:7]([OH:9])=[O:8])=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 184340291-Bromo-4-methoxy-2-phenylmethoxybenzeneHCID 178418339ButyllithiumHCID 178506736HCID 178506736, Verbindung

Produkt 1

HCID 152284862-(2-Benzyloxy-4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a THF (20 ml) solution of pyridine-2,3-dicarboxylic acid anhydride (1.92 g, 12.9 mmol) was added a THF solution of 2-benzyloxy-4-methoxyphenyllithium (10 ml), which was prepared from 2-benzyloxy-4-methoxyphenyl bromide (3.77 g, 12.9 mmol) and BuLi (1.6M hexane solution, 8.85 ml, 14.2 mmol) at -78° C., at -78° C. over a period of 5 min. The temperature of the mixture was raised to room temperature and the mixture was additionally stirred at the same temperature for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between 1N HCl and AcOEt. The organic layer was washed with 1N HCl, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in 1N NaOH and the solution was washed with AcOEt and chloroform. The aqueous layer was acidified with conc. HCl and extracted with AcOEt. The AcOEt layer was washed with 1N HCl and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was recrystallized from chloroform and chloroform-ether to give 2-(2-benzyloxy-4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid (2,03 g) as a colorless solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between 1N HCl and AcOEt
  3. washThe organic layer was washed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 1N NaOH
  8. washthe solution was washed with AcOEt and chloroform
  9. extractionextracted with AcOEt
  10. washThe AcOEt layer was washed with 1N HCl and brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was recrystallized from chloroform and chloroform-ether

Quellen und Nachweise

ORD-Eintrag
ord-23aa5b6e04ba4accbb6a67ef1ed9a05f
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714479

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