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Imidazole → 1-Allyloxycarbonyl-4-acetyl-2-tert-butyldimethylsilyloxymethyl-3-pyrroline

HRID 1029625
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1029625
C(Cl)Cl.[CH2:4]([O:7][C:8]([N:10]1[CH2:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][CH:11]1[CH2:18][OH:19])=[O:9])[CH:5]=[CH2:6].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C(OCC)(=O)C.O>[CH2:4]([O:7][C:8]([N:10]1[CH2:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][CH:11]1[CH2:18][O:19][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:9])[CH:5]=[CH2:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 199001161-Allyloxycarbonyl-4-acetyl-2-hydroxymethyl-3-pyrroline

Produkt 1

HCID 216468461-Allyloxycarbonyl-4-acetyl-2-tert-butyldimethylsilyloxymethyl-3-pyrrolineAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a methylene chloride solution (50 ml) of 1-allyloxycarbonyl-4-acetyl-2-hydroxymethyl-3-pyrroline (2.5 g) and imidazole (1.51 g) was added tert-butyldimethylsilyl chloride (2.5 g) under ice-cooling. The mixture was then stirred at room temperature for one day, followed by addition of water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate twice. The organic layers were combined, washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to give 1-allyloxycarbonyl-4-acetyl-2-tert-butyldimethylsilyloxymethyl-3-pyrroline (1.45 g).

Aufarbeitung

  1. temperaturecooling
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate twice
  4. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationFinally the solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-25b376efcccc4c77b972073ec6b979da
Quelldatensatz
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05102877

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