Sodium hydride → Tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate

HRID 1816557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816557
C(P([CH:7](C(C)C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(CC)=O)C.[H-].[Na+].[CH:18]([C:20]1[CH:21]=[CH:22][C:23]([O:33][CH3:34])=[C:24]([CH:32]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O.[Cl-].[NH4+]>O1CCCC1>[CH2:11]([O:10][C:8](=[O:9])[C:7]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:18][C:20]1[CH:21]=[CH:22][C:23]([O:33][CH3:34])=[C:24]([CH:32]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:12]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22494181Ethyl 2-(diethylphosphoryl)-2-isopropylacetateHCID 22494361Tert-butyl 5-formyl-2-methoxybenzoate

Produkt 1

HCID 69800512Tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoateAusbeute 162,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.6 g of ethyl 2-(diethylphosphoryl)-2-isopropylacetate was dissolved in 30 ml tetrahydrofuran, and 0.24 g of 60% sodium hydride was added thereto under ice-cooling. After stirring the reaction solution for 30 minutes under ice-cooling, 1.2 g of tert-butyl 5-formyl-2-methoxybenzoate was added, followed by stirring at room temperature for 3 hours. Aqueous ammonium chloride solution was added to the reaction mixture, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 1.5 g of tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate was obtained as an E-Z mixture.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 3 hours
  4. extractionby extracting with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. washfrom fractions eluted with hexane-ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-a678795e259b49d3889fa60c66fb0c67
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884821B1

Notizen zur Reaktion

Wird geladen…