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Hydrochloric Acid → Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate

HRID 1365043
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1365043
[O-]CC.[Na+].C(O[C:8](=[O:19])[C:9](=[CH:15]OCC)[C:10]([O:12][CH2:13][CH3:14])=[O:11])C.[CH:20]([NH:23][NH2:24])([CH3:22])[CH3:21].Cl>C(O)C.[Cl-].[Na+].O>[CH2:13]([O:12][C:10]([C:9]1[C:8]([OH:19])=[N:24][N:23]([CH:20]([CH3:22])[CH3:21])[CH:15]=1)=[O:11])[CH3:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 527891-IsopropylhydrazineHCID 2723922Sodium ethoxide

Produkt 1

HCID 178469772Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylateAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of sodium ethoxide (23 g) in ethanol (150 mL) were added ethoxymethylene malonic acid diethyl ester (32.7 g) and isopropylhydrazine (11.2 g) at room temperature, and the mixture was stirred at 80° C. for 4 hours and then at 100° C. for 2 hours. The reaction mixture was poured into 2 mol/L hydrochloric acid (300 mL), the mixture was diluted with brine and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (10.5 g).

Aufarbeitung

  1. waitat 100° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-6a10a2a426c840f8baa449f2a490249e
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07888487B2

Notizen zur Reaktion

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