Triethylamine → 1-Benzyl-3,5-dimethyl-1H-pyrazole

HRID 220464

Reaktionsgleichung

Reaktionsgleichung von HRID 220464
[CH3:1][C:2](=O)[CH2:3][C:4](=O)[CH3:5].Cl.Cl.[CH2:10]([NH:17][NH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)(=O)C>[CH2:10]([N:17]1[C:4]([CH3:5])=[CH:3][C:2]([CH3:1])=[N:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31261AcetylacetoneHCID 146540Benzylhydrazine dihydrochloride

Produkt 1

HCID 6037651-Benzyl-3,5-dimethyl-1H-pyrazoleAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Dissolve 2,4-pentanedione (5.09 g, 50.8 mmol) and benzylhydrazine dihydrochloride (10.91 g, 55.9 mmol) in acetic acid (40 mL). Slowly add triethylamine (15.6 mL, 0.112 mol) and stir the mixture for 18 hr. Concentrate the solution then dilute the residue with saturated aqueous sodium bicarbonate and extract 3 times with ethyl acetate. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 40:60 hexanes:ethyl acetate), to give 1-benzyl-3,5-dimethyl-1H-pyrazole as a yellow oil (8.703 g, 92%).

Aufarbeitung

  1. concentrationConcentrate the solution
  2. additionthen dilute the residue with saturated aqueous sodium bicarbonate
  3. extractionextract 3 times with ethyl acetate
  4. dry with materialDry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 40:60 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-adf012ae9ce445b39981d5845a2c7100
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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