Citric Acid → 1-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1778196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778196
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:25])[C:23]=1Br)=[O:18])[CH3:15].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(N(C)C)=O>[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:25])[C:23]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:18])[CH3:15]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 53302113Ethyl 5-Bromo-1-methyl-1H-pyrazole-4-carboxylate

Produkt 1

HCID 867185501-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Phenol (30.3 g; 322 mmol) is dissolved in DMA and K2CO3 (88.9 g; 643 mmol) is added portion wise. It is stirred for 10 minutes, then 5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (50.0 g; 215 mmol) is dropped to the reaction mixture and heated up to 140° C. for 16 hours. A 10% citric acid solution is added and extracted with DCM. The organic layer is washed with sodium bicarbonate and brine, then dried and purified through column chromatography.

Aufarbeitung

  1. extractionextracted with DCM
  2. washThe organic layer is washed with sodium bicarbonate and brine
  3. customdried
  4. custompurified through column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-61f03395f4d543b88452051962bba683
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266891B2

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