Sodium Iodide → Propan-2-yl 4-oxo-4-phenylbut-2-enoate

HRID 1981871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1981871
[C:1]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14](Br)([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[C:1]([CH:9]=[CH:10][C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 94714Beta-benzoylacrylic acid

Produkt 1

HCID 54289570Propan-2-yl 4-oxo-4-phenylbut-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3.52 g of 3-benzoylacrylic acid in 30 ml of dimethylformamide were added 8 ml of isopropylbromide, 5.5 g of potassium carbonate and a catalystic amount of sodium iodide. The mixture was stirred at room temperature for 4 hours and allowed to stand overnight. To the reaction solution was added water, the mixture was extracted with diethyl ether, and the diethyl ether layer was washed with water and dried over magnesium sulfate. The diethyl ether was removed from the solution by evaporation, and the residue was purified by silica gel column chromatography using a mixture of hexane and diethyl ether as an eluent to give 2.27 g of isopropyl 3-benzoylacrylate as an oil.

Aufarbeitung

  1. waitto stand overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. washthe diethyl ether layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe diethyl ether was removed from the solution by evaporation
  6. customthe residue was purified by silica gel column chromatography
  7. additiona mixture of hexane and diethyl ether as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-a5e70c8a8d9049f9a7c1edcbff2fb899
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04594197

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