Cesium carbonate → Methyl 3-(3-acetamidophenoxymethyl)-2-thiophenecarboxylate

HRID 1829

Reaktionsgleichung

Reaktionsgleichung von HRID 1829
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25]([O:27][CH3:28])=[O:26].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][CH2:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 121243-HydroxyacetanilideHCID 516892Sodium BicarbonateHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate

Produkt 1

HCID 19693072Methyl 3-(3-acetamidophenoxymethyl)-2-thiophenecarboxylateAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-acetamidophenol (4.79 g, 31.7 mmol) in dimethylformamide (50 ml) was added cesium carbonate (5.67 g, 17.4 mmol), followed by stirring at room temperature for 30 minutes. To the resulting mixture was added methyl 3-bromomethyl-2-thiophenecarboxylate (8.94 g, 38.0 mmol), and the mixture was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was poured into a 5% aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), followed by trituration with hexane to give methyl 3-(3-acetamidophenoxymethyl)-2-thiophenecarboxylate as a white solid (7.27 g, 75%).

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-29f57c2dee5f49d5a4d2fd451c9a7d4b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726325

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