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Cesium carbonate → 1-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinone

HRID 274941
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 274941
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2=[O:23])=[CH:4][C:3]=1[CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:34]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:35]([CH:34]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2=[O:23])=[CH:4][C:3]=1[CH2:24][CH2:25][CH3:26])([O:37][CH2:38][CH3:39])=[O:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 15383768Ethyl alpha-bromo-3,4-methylenedioxyphenylacetateHCID 200891871-(4-Hydroxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

Produkt 1

HCID 200891921-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinoneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 311
Citric Acid
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 0.105 g (0.30 mmol) of the product of step C in 1.0 mL of DMF was added 0.115 g (0.33 mmol) of cesium carbonate and the resulting suspension was stirred under a nitrogen atmosphere for 15 minutes. A solution of 0.094 g (0.33 mmol) ethyl α-bromo-3,4-methylenedioxyphenylacetate in 0.5 mL of DMF was then added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then suspended in 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane; combination of the product fractions and evaporation in vacuo afforded 0.137 g (83%) of the title compound.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 30% EtOAc-hexane
  10. customcombination of the product fractions and evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-15778c484e1741f39a1e7ba002b98059
Quelldatensatz
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05391566

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