Hydrochloric Acid → 3-tert-butyl-5-(2-phenylethyl)-1H-pyrazole

HRID 2110874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110874
[C:1]([C:5]1[CH:9]=[C:8]([CH:10]=O)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br-].[CH2:13]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O1CCCC1.[C].[Pd].CN(C)C=O>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2734970Benzyltriphenylphosphonium bromideHCID 1784410825-tert-Butyl-1H-pyrazole-3-carbaldehyde

Produkt 1

HCID 231573073-tert-butyl-5-(2-phenylethyl)-1H-pyrazoleAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

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

Versuchsvorschrift

A mixture of 3-tert-butyl-1H-pyrazole-5-carbaldehyde (1.52 g, 10.0 mmol), benzyltriphenylphosphonium bromide (6.50 g, 15.0 mmol), potassium carbonate (2.76 g, 20.0 mmol) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 14 hr. The reaction mixture was poured into 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (5%-80% ethyl acetate/hexane) to give pale-yellow crystals. The obtained crystals were dissolved in a mixed solvent of ethanol (50 mL) and tetrahydrofuran (50 mL), and 10% palladium-carbon (50% water-containing product, 2.0 g) was added. The mixture was stirred under an atmospheric hydrogen atmosphere for 3 hr. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (1.90 g, yield 83%) as colorless crystals. 1H NMR (CDCl3) δ: 1.31 (9H, s), 2.90-2.99 (4H, m), 5.89 (1H, s), 7.18-7.33 (5H, m).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography (5%-80% ethyl acetate/hexane)
  4. customto give pale-yellow crystals
  5. additionwas added
  6. stirringThe mixture was stirred under an atmospheric hydrogen atmosphere for 3 hr
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-25cbb04f9fd3418db28602e09612e77f
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517910B2

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