Citric Acid → 4-(4-chlorobenzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid

HRID 1909867

Reaktionsgleichung

Reaktionsgleichung von HRID 1909867
[H-].[Na+].[O:3]1[C:10]2[CH:9]=[C:8]([C:11]([O:13]C)=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:7]2[C:8]([C:11]([OH:13])=[O:12])=[CH:9][C:10]3[O:3][CH:4]=[CH:5][C:6]2=3)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylate

Produkt 1

HCID 397337984-(4-chlorobenzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acidAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of sodium hydride (0.29 g, 55% dispersion in paraffin liquid) and DMF (10 mL) was added methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (0.5 g) under ice-cooling, followed by stirring for 10 minutes and further 1-(bromomethyl)-4-chlorobenzene (0.81 g) was added thereto, followed by stirring at room temperature for 4 hours. To the reaction mixture was added a 10% aqueous citric acid solution (10 mL), followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate: 5/1-3/1) to obtain 4-(4-chlorobenzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid (0.35 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring at room temperature for 4 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate: 5/1-3/1)

Quellen und Nachweise

ORD-Eintrag
ord-147052373a9a4f6f922197eb55206b96
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598355B2

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