Potassium Carbonate → Ethyl 2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 2389873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2389873
[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]2[O:21][CH2:22][CH2:23][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]([O:36][CH2:37][CH3:38])(=[O:35])[C:31]#[C:32][CH2:33][CH3:34]>CN(C)C=O.O>[CH2:33]([C:32]1[C:31]([C:30]([O:36][CH2:37][CH3:38])=[O:35])=[C:16]2[C:17]3[CH2:23][CH2:22][O:21][C:18]=3[CH:19]=[CH:20][N:15]2[N:14]=1)[CH3:34]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 99169Ethyl pent-2-yn-1-oateHCID 866386665-Amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

Produkt 1

HCID 53310990Ethyl 2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylateAusbeute 12,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 5-amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (8.00 g, 25.0 mmol) and potassium carbonate (4.84 g, 35.0 mmol) in dimethylformamide (100 mL) was added ethyl 2-pentynoate (3.63 mL, 27.5 mmol) under ice-cooling, and the mixture was stirred at room temperature for 20 hr. The reaction solution was diluted with water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (794 mg, yield 12%).

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Quellen und Nachweise

ORD-Eintrag
ord-77e41a38727442d5b246fcbb81e7012c
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273761B2

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