18-Crown-6 → HCID 86658558, Verbindung

HRID 1520204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520204
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14]Br)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[F-:19].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14][F:19])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 866423312-Bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethanone

Produkt 1

HCID 86658558HCID 86658558, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

According to Scheme 6 Step 1: A solution of 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromoethanone (8.39 mmol, 3.00 g), KF (33.6 mmol, 1.97 g) and 18-crown-6 (4.20 mmol, 1.12 g) in acetonitrile (25 mL) was stirred under reflux for 3 hours. After the evaporation of solvent, the crude residue was dissolved in AcOEt. The organic phase was washed with water, was dried over Na2SO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 95:5) as eluent to yield 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-fluoroethanone (3.62 mmol, 900 mg, 78%) as a white solid.

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. customAfter the evaporation of solvent
  3. dissolutionthe crude residue was dissolved in AcOEt
  4. washThe organic phase was washed with water
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated
  8. customThe resulting crude product was purified by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4ce6190fff7a4f37b1ba1b76a7d7e80d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073907B2

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