Tetrahydrofuran → 3-Pyridinecarboxylic acid, 2-(4-methoxybenzoyl)-

HRID 274216

Reaktionsgleichung

Reaktionsgleichung von HRID 274216
C1COCC1.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([O:14][C:15](=[O:16])[C:7]=12)=[O:13].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1.[NH4+].[Cl-]>Cl>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:15]([C:7]2[C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=[CH:11][N:6]=2)=[O:16])=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 178491912HCID 178491912, Verbindung

Produkt 1

HCID 113343683-Pyridinecarboxylic acid, 2-(4-methoxybenzoyl)-Ausbeute 27,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a THF (15 ml) solution of pyridine-2,3-dicarboxylic acid anhydride (1.0 g, 6.7 mmol) was added dropwise a THF solution of 4-methoxyphenylmagnesium bromide (0.89M, 8.0 ml, 7.1 mmol) at -78° C. The reaction mixture was stirred at the same temperature for 1 h and then a saturated aqueous solution of NH4Cl (20 ml) was added to quench the reaction. The reaction mixture was diluted with 1N HCl and extracted with AcOEt. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (E. Merck, Kieselgel 60/chloroform:methanol=10:1) to give 2-(4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid (479 mg) as a colorless solid.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (E. Merck, Kieselgel 60/chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-b52f5b32182147ada5b88506affe7b8f
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389620

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