2-Acetylpyrrole → 2-Acetyl-1-(4-fluorobenzyl)pyrrole

HRID 479438

Reaktionsgleichung

Reaktionsgleichung von HRID 479438
[H-].[Na+].[C:3]([C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)(=[O:5])[CH3:4].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>CN(C=O)C>[C:3]([C:6]1[N:7]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 140792-AcetylpyrroleHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromide

Produkt 1

HCID 4926932-Acetyl-1-(4-fluorobenzyl)pyrroleAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 1.32 g, 33 mmol) in DMF (30 ml) was added at an ice bath temperature a solution of 2-acetylpyrrole (3.27 g, 30 mmol) in DMF (5 ml). The mixture was stirred at room temperature for 15 minutes and cooled again. To the solution was added dropwise a solution of 4-fluorobenzylbromide (6.24 g, 33 mmol) in DMF (2 ml). The reaction solution was stirred at room temperature for 1 hour and poured into ice-water, and then extracted with ethylacetate. The ethyl acetate was washed with water and dried. The solvent was evaporated to give 2-acetyl-1-(4-fluorobenzyl)pyrrole (6.5 g) as an oil quantitatively.

Aufarbeitung

  1. temperaturecooled again
  2. stirringThe reaction solution was stirred at room temperature for 1 hour
  3. extractionextracted with ethylacetate
  4. washThe ethyl acetate was washed with water
  5. customdried
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-3dd2b0d6dc40443ba23d49825ded52f1
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645956B1

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