Tetrabutylammonium Fluoride → 1-(4-hydroxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl)ethanone

HRID 2273305

Reaktionsgleichung

Reaktionsgleichung von HRID 2273305
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:33](=[O:35])[CH3:34])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][CH2:19][C:20]1[N:21]=[C:22]([C:33](=[O:35])[CH3:34])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:24]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 710876851-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

Produkt 1

HCID 710869721-(4-hydroxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl)ethanoneAusbeute 108,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The compound obtained in (2) (24.4 g) was dissolved in THF (200 mL), tetrabutylammonium fluoride (hereinafter sometimes referred to as TBAF) (a 1.0 M THF solution, 62.7 mL) was added under stirring, and stirring was continued for 1 hour. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→100%) using an amino column (trade name: Hi-Flash Column 5L Amino, manufactured by Yamazen Corporation) to give the title compound (14.1 g).

Aufarbeitung

  1. additionwas added
  2. stirringstirring
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→100%)

Quellen und Nachweise

ORD-Eintrag
ord-be9491f77dfe4d37ad5c878abb97daf5
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120835B2

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