Sodium Chloride → Ethyl 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylate

HRID 2427406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427406
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH3:19])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])[CH3:4].[CH3:20]I.[Na+].[Cl-]>C1COCC1.O.C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH3:20])[CH:10]=[C:11]([CH3:19])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])[CH3:4]

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107045911H-Pyrrole-2-carboxylic acid, 4-methyl-3-phenyl-, ethyl ester

Produkt 1

HCID 378982Ethyl 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (436 mg, 60% in mineral oil, 10.9 mmol) was added to a solution of 4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.25 g, 5.45 mmol) in THF (10 mL) at 0° C. and under nitrogen as inert gas and the reaction mixture was stirred for 15 min. Then methyl iodide (1,547 g, 10.9 mmol) was added to the reaction mixture and the reaction mixture was stirred for 1 h at 0° C. and overnight at RT. After the addition of a few drops of water and aq. sat. NaCl solution (250 mL), extraction was performed with DCM (2×250 mL). After drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification was performed by means of column chromatography. The desired product 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.02 g, 77% of theoretical) was obtained.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 1 h at 0° C. and overnight at RT
  2. dry with materialAfter drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification

Quellen und Nachweise

ORD-Eintrag
ord-3d9e80c908304864a84186d00d951c29
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968591B2

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