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Acetic Acid → 2-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

HRID 351258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 351258
[F:1][C:2]([F:18])([F:17])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1)=O.Cl.[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1)([O-:22])=[O:21].[CH3:31][C:32](O)=[O:33]>O>[C:32]([O:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:29]([C:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:28][CH:27]=3)[N:30]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)=[CH:8][CH:9]=1)(=[O:33])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 54634014-Nitrophenylhydrazine hydrochlorideHCID 210909544,4,4-Trifluoro-1-[4-(2-hydroxy-ethyl)phenyl]-1,3-butanedione

Produkt 1

HCID 210907432-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4,4,4-trifluoro-1-[4-(2-hydroxy-ethyl)phenyl]-1,3-butanedione (670 mg) and (4-nitrophenyl)hydrazine hydrochloride (439 mg) in AcOH (5 ml) and H2O (0.5 ml) was stirred at ambient temperature overnight. The mixture was concentrated in vacuo, and the residue was partitioned between AcOEt and 1M HCl. The organic layer was washed with 1M HCl for two times, saturated aqueous sodium bicarbonate solution for three times, and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=10% and 15% to give 2-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate (501 mg) as an oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between AcOEt and 1M HCl
  3. washThe organic layer was washed with 1M HCl for two times, saturated aqueous sodium bicarbonate solution for three times, and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with AcOEt/n-hexane=10% and 15%

Quellen und Nachweise

ORD-Eintrag
ord-fe24ce61ef9646d38c28aae168c4e2e5
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07183306B2

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