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

HRID 79308

Reaktionsgleichung

Reaktionsgleichung von HRID 79308
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:1]2[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]2)=[CH:14][CH:15]=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 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To ethyl 1H-pyrazole-4-carboxylate (5.01 g, 35.7 mmol) in DMF (60 mL) was added 1-(chloromethyl)-4-methoxybenzene (6.16 g, 39.3 mmol) and K2CO3 (7.41 g, 53.6 mmol). The reaction mixture was stirred for 16 hours and concentrated under reduced pressure to remove DMF. The residue was diluted with EtOAc (100 mL), washed with H2O (30 mL) and brine (20 mL), dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/hexanes 1:5) provided the desired product (8.31 g).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customto remove DMF
  3. additionThe residue was diluted with EtOAc (100 mL)
  4. washwashed with H2O (30 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4a325198d1ef4226adffc2dd3c2b197a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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