Acetic Acid → ethyl 5-(2-hydroxy-2-methylpropyl)-1-propyl-1H-pyrazole-3-carboxylate

HRID 1095372

Reaktionsgleichung

Reaktionsgleichung von HRID 1095372
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[Na+].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[C:8](OCC)=O.[C:17](O)(=O)[CH3:18].C(O)(=O)C(O)=O.[CH2:27]([NH:30][NH2:31])[CH2:28][CH3:29]>C(O)C>[OH:4][C:2]([CH3:5])([CH3:3])[CH2:1][C:17]1[N:30]([CH2:27][CH2:28][CH3:29])[N:31]=[C:8]([C:7]([O:14][CH2:15][CH3:16])=[O:13])[CH:18]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 96079Hydrazine, propyl-, ethanedioate (1:1)HCID 23676156Sodium t-butoxide

Produkt 1

HCID 66781950ethyl 5-(2-hydroxy-2-methylpropyl)-1-propyl-1H-pyrazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of sodium tert-butoxide dissolved in ethanol (71 mL) was added diethyl oxalate (16.1 g, 110 mmol) followed by the material obtained in Part A (18.8 g, 100 mmol). The reaction was stirred 30 minutes at ambient temperature before cooling to 0° C. and adding acetic acid (100 mL) and propylhydrazine oxalate (16.4 g, 100 mmol). The reaction was allowed to warm to ambient temperature and stirred for 19 hours. The solvent was removed under reduced pressure. The resulting brown oil was purified by automated flash chromatography (AnaLogix, eluting with a gradient of 50-75% ethyl acetate in hexanes) to provide 9.6 g of ethyl 5-(2-hydroxy-2-methylpropyl)-1-propyl-1H-pyrazole-3-carboxylate as a yellow oil.

Aufarbeitung

  1. customobtained in Part A (18.8 g, 100 mmol)
  2. temperaturebefore cooling to 0° C.
  3. temperatureto warm to ambient temperature
  4. stirringstirred for 19 hours
  5. customThe solvent was removed under reduced pressure
  6. customThe resulting brown oil was purified by automated flash chromatography (AnaLogix
  7. washeluting with a gradient of 50-75% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0beb1909aaac4e39a96bf49c09c5c581
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138173B2

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