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Water → Diethyl 2-acetoxymethyl-1-benzylimidazole-4,5-dicarboxylate

HRID 53057
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 53057
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6]([N:13]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:15]=[C:14]1[CH2:28]Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.O>CN(C)C=O>[C:1]([O:4][CH2:28][C:14]1[N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:15]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 19036091Diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate

Produkt 1

HCID 19036167Diethyl 2-acetoxymethyl-1-benzylimidazole-4,5-dicarboxylateAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1.11 g of sodium acetate were added to a solution of 2.67 g of diethyl11-benzyl-2-bromomethylimidazole-4,5-dicarboxylate [prepared as described in Preparation 42(ii)] in 30 ml of dimethylformamide, and the resulting mixture was heated at 40° C. for 5 hours. At the end of this time, the reaction solution was mixed with ethyl acetate and water, and then the ethyl acetate layer was separated. The resulting ethyl acetate extract was washed with an aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.52 g of the title compound as a syrup.

Aufarbeitung

  1. customthe ethyl acetate layer was separated
  2. extractionThe resulting ethyl acetate extract
  3. washwas washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-f2d180ee8446400f906080597addea0d
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05616599

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