Pentenone → ethyl 4,5-dihydro-3,5-dimethyl-1H-pyrazole-1-acetate

HRID 1916445

Reaktionsgleichung

Reaktionsgleichung von HRID 1916445
Cl.[NH:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:3].[CH3:10][C:11](=O)[CH:12]=[CH:13][CH3:14].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:10][C:11]1[CH2:12][CH:13]([CH3:14])[N:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:3]=1

Komponenten

5

Edukt 3

HCID 12248PentenoneHCID 516892Sodium BicarbonateHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 67378927ethyl 4,5-dihydro-3,5-dimethyl-1H-pyrazole-1-acetateAusbeute 14,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl hydrazinoacetate hydrochloride (1.55 g, 10 mmol), 3-pentene-2-one (0.95 mL, 10 mmol) and sodium bicarbonate (1.00 g, 11.9 mmol) in ethanol (10 mL) was stirred at room temperature overnight. The reaction mixture was then filtered and concentrated under reduced pressure. The resulting oil was purified by medium pressure liquid chromatography on silica gel (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a yellow oil (0.26 g).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting oil was purified by medium pressure liquid chromatography on silica gel (0 to 100% gradient of ethyl acetate in hexanes as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-cef1dd2f91c74bdc98647778372a4bf9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618137B2

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