Potassium Carbonate → Ethyl 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1893707

Reaktionsgleichung

Reaktionsgleichung von HRID 1893707
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]([F:20])([F:19])[C:9]1[NH:13][N:12]=[CH:11][C:10]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>C(#N)C>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:12]2[CH:11]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([C:8]([F:7])([F:19])[F:20])=[N:13]2)=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 596095Ethyl 3-(Trifluoromethyl)pyrazole-4-carboxylate

Produkt 1

HCID 58243468Ethyl 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

According to Scheme 1, Step 1: K2CO3 (11.5 mmol, 1.59 g) was added to a solution of ethyl 5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (7.69 mmol, 1.60 g) in acetonitrile (24 mL) followed by 1-(chloromethyl)-4-methoxybenzene (8.46 mmol, 1.15 mL) and the reaction mixture was heated under reflux for 4.5 hours. After evaporation of the solvent, the reaction mixture was diluted with brine and EtOAc. The aqueous phase was extracted with EtOAc. The organic phase was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield ethyl 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (7.68 mmol, 2.52 g, 100%) as an oil.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 4.5 hours
  3. customAfter evaporation of the solvent
  4. additionthe reaction mixture was diluted with brine and EtOAc
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationwas filtered
  8. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-73ab3297903d4f4bba538b80801b4cfe
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513252B2

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