3-Phenylprop-2-Enal → N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamide

HRID 2226283

Reaktionsgleichung

Reaktionsgleichung von HRID 2226283
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:15]([CH2:22][CH3:23])[C:16](=[O:21])[CH2:17][C:18]([CH3:20])=[O:19])[CH3:14].[CH:24](=[O:33])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CCCCCC.O>[CH2:22]([N:15]([CH2:13][CH3:14])[C:16](=[O:21])[CH2:17][C:18](=[O:19])[CH2:20][CH:24]([OH:33])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:23]

Komponenten

8

Edukt 5

HCID 3073-Phenylprop-2-EnalHCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 16699Acetoacetamide, N,N-diethyl-HCID 178418339Butyllithium

Produkt 1

HCID 54551573N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

2.65 cm3 of diisopropylamine are introduced into a three-necked, round-bottomed flask equipped with a septum and a dropping funnel and are then cooled to -10° C. 10.4 cm3 of n-butyllithium in solution in hexane at 1.6 mol/liter (16.6 mmol) are then slowly added and the mixture is then stirred for 15 minutes. 1.40 g of N,N-diethylacetoacetamide (8.65 mmol) are then slowly added and the mixture is then stirred for 15 minutes. 1.0 g of cinnamaldehyde (7.57 mmol) is added. The mixture is stirred for 25 minutes and then 2 cm3 of concentrated hydrochloric acid and 25 cm3 of water are added. Extraction is carried out with 2 times 25 cm3 of dichloromethane. The combined organic phases are washed with 4 times 50 cm3 of water and dried over sodium sulphate. After filtration and concentration to dryness, there is obtained, with a yield of 85%, 1.86 g of N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamide, the structure of which is confirmed by the proton nuclear magnetic resonance spectrum.

Aufarbeitung

  1. customequipped with a septum and a dropping funnel
  2. stirringthe mixture is then stirred for 15 minutes
  3. stirringThe mixture is stirred for 25 minutes
  4. extractionExtraction
  5. washThe combined organic phases are washed with 4 times 50 cm3 of water
  6. dry with materialdried over sodium sulphate
  7. filtrationAfter filtration and concentration to dryness

Quellen und Nachweise

ORD-Eintrag
ord-95093fd6497e4ee48aa08e1bc1812b82
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05347039

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