Water → 5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole

HRID 507923

Reaktionsgleichung

Reaktionsgleichung von HRID 507923
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([CH:14]=O)[NH:11][N:10]=2)=[CH:5][CH:4]=1.[Br-].[CH2:19]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.O1CCCC1.C(O)C.[C].[Pd]>[C:20]1([CH2:19][CH2:14][C:12]2[NH:11][N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=3)[CH:13]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734970Benzyltriphenylphosphonium bromideHCID 231574743-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbaldehyde

Produkt 1

HCID 231573735-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazoleAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-[4-(Trifluoromethyl)phenyl]-1H-pyrazole-5-carbaldehyde (1.20 g, 5.0 mmol) was dissolved in N,N-dimethylformamide (10 mL), and benzyltriphenylphosphonium bromide (3.25 g, 7.5 mmol) and potassium carbonate (2.76 g, 20.0 mmol) were added. The mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (10%-65% ethyl acetate/hexane) to give colorless crystals. The colorless crystals were dissolved in tetrahydrofuran (30 mL) and ethanol (30 mL), and 10% palladium-carbon (50% water-containing product, 500 mg) was added. Under an atmospheric hydrogen atmosphere, the mixture was stirred at room temperature for 2 hr. The catalyst was filtered off, and the filtrate was concentrated to give the title compound (880 mg, yield 56%, 2 steps) as colorless crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (10%-65% ethyl acetate/hexane)
  5. customto give colorless crystals
  6. stirringUnder an atmospheric hydrogen atmosphere, the mixture was stirred at room temperature for 2 hr
  7. filtrationThe catalyst was filtered off
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-cb846fcb1a614538a7e44b1f8fc6614b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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