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Imidazole → HCID 14802197, Verbindung

HRID 2351007
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2351007
[OH:1][C:2]1[C:3]([CH3:13])=[C:4]([CH3:12])[C:5]2[O:9][CH2:8][S:7][C:6]=2[C:10]=1[CH3:11].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C=O>[Si:19]([O:1][C:2]1[C:3]([CH3:13])=[C:4]([CH3:12])[C:5]2[O:9][CH2:8][S:7][C:6]=2[C:10]=1[CH3:11])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13592053HCID 13592053, Verbindung

Produkt 1

HCID 14802197HCID 14802197, VerbindungAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

0.84 g of 5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 64) was dissolved in 5 ml of dimethylformamide, and then 0.58 g of imidazole and 1.29 g of t-butyldimethylsilyl chloride were added to the resulting solution. The mixture was then stirred for 7 hours at 50° C., after which it was allowed to stand overnight at room temperature. The solvent was then distilled off under reduced pressure, and the residue was extracted with benzene. The extract was washed with a saturated aqueous solution of sodium bicarbonate and with water, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The resulting residue was subjected to column chromatography through 40 g of silica gel eluted with hexane and with mixtures of hexane and benzene ranging from 10:1 to 2:1 by volume, to yield 1.26 g of the title compound as a colorless oily substance.

Aufarbeitung

  1. waitto stand overnight at room temperature
  2. distillationThe solvent was then distilled off under reduced pressure
  3. extractionthe residue was extracted with benzene
  4. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate and with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off
  7. washeluted with hexane and with mixtures of hexane and benzene ranging from 10:1 to 2:1 by volume

Quellen und Nachweise

ORD-Eintrag
ord-c679d4af40ca4223b2738945ee6be579
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04871762

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