4,4,4-Trifluoro-1-phenyl-1,3-butanedione → 2-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891063

Reaktionsgleichung

Reaktionsgleichung von HRID 891063
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1)[NH2:3].[C:13]([CH2:21][C:22](=O)[C:23]([F:26])([F:25])[F:24])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([C:13]2[N:2]([C:4]3[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][OH:12])=[CH:8][CH:9]=3)[N:3]=[C:22]([C:23]([F:24])([F:25])[F:26])[CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 222447112-(4-Hydrazinophenyl)ethanol hydrochloride

Produkt 1

HCID 222445582-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanolAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-hydrazinophenyl)ethanol hydrochloride (J. Med. Chem., 1999, 42, 2504, 202 mg, 1.07 mmol) and benzoyl-1,1,1-trifluoroacetone (278 mg, 1.28 mmol) in ethanol (13 mL) was heated under reflux overnight. After removal of the solvent, the resulting residue was partitioned between dichloromethane and water. Organic phase was washed with brine and dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 200 mg (56%) of the title compound as yellow solids: MS (ESI) m/z 333 [M+H]+, 1H-NMR (CDCl3) δ 7.36-7.20 (9H, m), 6.74 (1H, s), 3.86 (2H, br.s), 2.89 (2H, t, J=6.6 Hz).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customAfter removal of the solvent
  4. customthe resulting residue was partitioned between dichloromethane and water
  5. washOrganic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customAfter removal of the solvent
  8. customthe crude product was purified by TLC with hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9e07c64372314e6692139765531f2263
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001917B2

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