Ethyl bromoacetate → (3-Methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester

HRID 1786230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786230
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]1=[O:1])[CH3:15]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178426317HCID 178426317, Verbindung

Produkt 1

HCID 22943407(3-Methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-3-methyl-pyridine (4.1 g, 37 mmol), ethyl bromoacetate (5.9 g, 35 mmol) and potassium carbonate (4.9 g, 35 mmol) in DMF (60 ml) was stirred at rt for 16 h. After evaporation of the solvent and extractive workup (ethyl acetate/water) the organic phase was concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 40:60). The title compound elutes as the second product and was isolated as a colorless liquid (6.1g, 84%). MS: m/e=196.0[M+H]+.

Aufarbeitung

  1. customAfter evaporation of the solvent and extractive workup (ethyl acetate/water) the organic phase
  2. concentrationwas concentrated
  3. customchromatographed (SiO2, heptane:ethyl acetate=100:0 to 40:60)

Quellen und Nachweise

ORD-Eintrag
ord-240c2c563c7543ad9d8e9928e954eff1
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507729B2

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