Hydrazine hydrate (1:1) → ethyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

HRID 386342

Reaktionsgleichung

Reaktionsgleichung von HRID 386342
[C:1]([CH:4]([C:11](=O)[CH3:12])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2].O.[NH2:15][NH2:16]>C(O)C>[CH3:2][C:1]1[C:4]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:11]([CH3:12])[NH:16][N:15]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 87820Ethyl 3-acetyl-4-oxopentanoate

Produkt 1

HCID 16394806ethyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 3-acetyl-4-oxopentanoate (synthesized as described D. P. Shrout and D. A. Lightner, Synth. Commun. 20 (1990), 2075) (9.676 g, 51.96 mmol) in ethanol, at 0° C., was added slowly a solution of hydrazine hydrate (2.990 g, 59.75 g) in absolute ethanol. The reaction mixture was warmed to room temperature and stirred for 2 hours. After removing ethanol under vacuum, dichloromethane and water were added to the crude product and the organic layer was separated. The aqueous layer was extracted further with dichloromethane and the combined organic extracts were washed with water. After drying over MgSO4 and evaporation of the solvent under reduced pressure, the pyrazole was isolated as a yellow oil. Yield: 72% (6.777 g, 37.2 mmol).

Aufarbeitung

  1. customAfter removing ethanol under vacuum, dichloromethane and water
  2. additionwere added to the crude product
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted further with dichloromethane
  5. washthe combined organic extracts were washed with water
  6. dry with materialAfter drying over MgSO4 and evaporation of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9c886412d52e4145be71feddcd8fb175
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372379B2

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