1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 1-ethyl-4-fluoro-2-naphthalen-1-yl-1H-imidazole

HRID 12467

Reaktionsgleichung

Reaktionsgleichung von HRID 12467
[CH2:1]([N:3]1[C:7]([Si](C)(C)C)=[C:6]([F:12])[N:5]=[C:4]1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([N:3]1[CH:7]=[C:6]([F:12])[N:5]=[C:4]1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 686294501-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole

Produkt 1

HCID 593377711-ethyl-4-fluoro-2-naphthalen-1-yl-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Crude 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole (5.49 g) is dissolved in THF (75 ml), and to the solution is added tetrabutylammonium fluoride hydrate (5.4 g, 20.6 mmol, 1.2 eq.). The resulting mixture is stirred at rt for 4 hr. The organic solvent is evaporated under reduced pressure, and the residue is dissolved in EtOAc (150 ml), washed with water and brine, and dried over Na2SO4. Concentration and purification through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1) affords 1-ethyl-4-fluoro-2-naphthalen-1-yl-1H-imidazole. LCMS 241 (M+1).

Aufarbeitung

  1. customThe organic solvent is evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in EtOAc (150 ml)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and purification through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-a55c86c65da04b15a979060a6498a635
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728009B1

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