Tetrabutylammonium Fluoride → HCID 22291371, Verbindung

HRID 967815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967815
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[C:18]2[CH2:28][CH3:29])=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:28]([C:18]1[N:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][OH:8])=[CH:16][CH:15]=2)[CH:21]=[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:19]=1)[CH3:29]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 69693476HCID 69693476, Verbindung

Produkt 1

HCID 22291371HCID 22291371, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole (1.84 g, 4.6 mmol) in tetrahydrofuran (25 mL) was added tetrabutylammonium fluoride (1.84 g, 6.9 mmol) at 0° C. After 1 h, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:1) to afford 1.44 g (quant) of the title compound as colorless amorphous : MS (ESI) m/z 293 [M+H]+1H-NMR (CDCl3)δ1.26 (3H, t, J=7.5 Hz), 2.72 (2H, q, J=7.5 Hz), 2.95 (2H, t, J=6.6 Hz), 3.93 (2H, t, J=6.6 Hz), 7.22-7.28 (4H, m), 7.34-7.41 (4H, m), 7.79 (2H, d, J=7.1 Hz).

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-8c602aea1e6a4f3087985e551dc18551
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956050B2

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