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Acetic Acid → 4-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

HRID 2037178
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2037178
CCO[C:4]([C:6]([CH2:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])=[O:7])=[O:5].[S:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)=[CH:16]1.[CH3:27][O:28][C:29]([CH2:31][O:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O)=[O:30].C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Cl-].[Na+].O.O1CCOCC1>[CH3:14][C:11]([CH3:12])([CH3:13])[C:9]([C:8]1[CH:35]([C:34]2[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=2[O:32][CH2:31][C:29]([O:28][CH3:27])=[O:30])[N:24]([C:23]2[CH:25]=[CH:26][C:20]([C:17]3[CH:18]=[CH:19][S:15][CH:16]=3)=[CH:21][CH:22]=2)[C:4](=[O:5])[C:6]=1[OH:7])=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoateHCID 516892Sodium BicarbonateHCID 41303364-(Thiophen-3-yl)anilineHCID 5151625Methyl 2-(2-formylphenoxy)acetate

Produkt 1

HCID 58365329
4-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one
Ausbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of ethyl trimethylacetopyruvate (0.40 g, 2 mmol), 4-thiophene-3-ylaniline (0.35 g, 2 mmol), 2-(methoxycarbonylmethyloxy)benzaldehyde (0.39, 2 mmol), acetic acid (0.057 mL, 1 mmol) and dioxane (4 mL) was heated at reflux overnight. After the reaction was completed, saturated sodium bicarbonate solution and brine were poured into the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulphate, and then concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform), and the aimed compound was triturated with ethyl acetate and diisopropyl ether to give 4-(2,2-dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.42 g, yield: 41%) as pale brown solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified on a silica gel column chromatography (methanol/chloroform)
  7. customthe aimed compound was triturated with ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-fc4b6fe35cc742499ecf0cff7786da40
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575197B2

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