Acetic Anhydride → Ethyl 1-phenyl-3-pyrrolecarboxylate

HRID 2292842

Reaktionsgleichung

Reaktionsgleichung von HRID 2292842
[CH:1]([N:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][C:5](O)=O)=O.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[C:15]#C.C(OC(=O)C)(=O)C>CCCCCC>[C:8]1([N:3]2[CH:4]=[CH:5][C:15]([C:14]([O:18][CH2:19][CH3:20])=[O:17])=[CH:1]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 12182Ethyl propiolateHCID 7099130(Formylanilino)acetic acid

Produkt 1

HCID 22738020Ethyl 1-phenyl-3-pyrrolecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A mixture of 2.69 g (15 mmole) of N-formyl-N-phenyl-glycine prepared in Reference Example 3, 5.47 g (55.8 mmole) of ethyl propiolate, and 15 ml of acetic anhydride was stirred using a magnetic stirrer over an oil bath at 130° C. for 22 hours. The reaction mixture was concentrated under vacuum. 22 ml of toluene was added to the residue and the mixture was evaporated under reduced pressure. This procedure was repeated to obtain a brown oily substance. This oily substance was purified using silica gel column chromatography (No. 9385 silica gel, manufactured by Merck Co., eluted with ethyl acetate:hexane=1:5 v/v) to obtain 2.8949 (yield 89.6%) of a light-yellow oil of the title compound.

Aufarbeitung

  1. customat 130° C.
  2. customfor 22 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. addition22 ml of toluene was added to the residue
  5. customthe mixture was evaporated under reduced pressure
  6. customto obtain a brown oily substance
  7. customThis oily substance was purified
  8. wash, eluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-79c22996605c4231a1a6f9a9954cc030
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684161

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