Triethylamine → ethyl 1-butyl-5-methyl-1H-pyrazole-3-carboxylate

HRID 1984330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984330
C(O)(=O)C(O)=O.[CH2:7]([NH:11][NH2:12])[CH2:8][CH2:9][CH3:10].O=[C:14]([CH2:20][C:21](=O)[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>C(O)C>[CH2:7]([N:11]1[C:21]([CH3:22])=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12]1)[CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 69208Ethyl 2,4-dioxovalerateHCID 162021Butylhydrazine oxalate

Produkt 1

HCID 66958271ethyl 1-butyl-5-methyl-1H-pyrazole-3-carboxylateAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Butylhydrazine oxalate (25 g, 140 mmol) was added over a period of 15 minutes to a solution of ethyl 2,4-dioxovalerate (22.2 g, 140 mmol) and triethylamine (210 mmol) in ethanol (140 mL). The resulting solution was stirred overnight at ambient temperature and concentrated under reduced pressure. Hexane was added, and an insoluble solid was removed by filtration. The hexane was removed under reduced pressure; the residue was purified by chromatography on a HORIZON HPFC system (65I cartridge, eluting with hexanes/ethyl acetate in a gradient from 80:20 to 45:55) to provide 18.1 g of ethyl 1-butyl-5-methyl-1H-pyrazole-3-carboxylate as a pale yellow oil.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionHexane was added
  3. customan insoluble solid was removed by filtration
  4. customThe hexane was removed under reduced pressure
  5. customthe residue was purified by chromatography on a HORIZON HPFC system (65I cartridge
  6. washeluting with hexanes/ethyl acetate in a gradient from 80:20 to 45:55)

Quellen und Nachweise

ORD-Eintrag
ord-9eeb3390587c4c2c8fba261fdc6af33e
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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