Potassium Carbonate → ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate

HRID 1910841

Reaktionsgleichung

Reaktionsgleichung von HRID 1910841
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[NH:17]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[N:18]1>C(#N)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:17]2[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[N:18]2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 142179ethyl 1H-pyrazole-4-carboxylate

Produkt 1

HCID 44558860ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

According to Scheme 1 Step 1: K2CO3 (803 mmol, 111 g) followed by 1-(chloromethyl)-4-methoxybenzene (562 mmol, 76.0 mL) were added slowly to a solution of ethyl 1H-pyrazole-4-carboxylate (535 mmol, 75.0 g) in acetonitrile (500 mL) at room temperature. Then the suspension was heated under reflux for 4 hours. At room temperature, the reaction mixture was filtered, was concentrated under reduced pressure and was slurried in petroleum ether to yield ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (530 mmol, 138 g, 99%) as a white solid.

Aufarbeitung

  1. temperatureThen the suspension was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationAt room temperature, the reaction mixture was filtered
  4. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c9177c6e9b564565b92b84ee5b12a27b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604033B2

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