Benzaldehyde → N,N-diethyl-5-phenyl-5-hydroxy-3-oxopentanamide

HRID 2226281

Reaktionsgleichung

Reaktionsgleichung von HRID 2226281
[H-].[Na+].[CH2:3]([N:5]([CH2:12][CH3:13])[C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9])[CH3:4].C([Li])CCC.[CH:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O1CCCC1.CCCCCC.O>[CH2:12]([N:5]([CH2:3][CH3:4])[C:6](=[O:11])[CH2:7][C:8](=[O:9])[CH2:10][CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[OH:26])[CH3:13]

Komponenten

9

Edukt 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 16699Acetoacetamide, N,N-diethyl-HCID 24758Sodium hydrideHCID 178418339Butyllithium

Produkt 1

HCID 18967271N,N-diethyl-5-phenyl-5-hydroxy-3-oxopentanamideAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

1.53 g of 80% sodium hydride (51.0 mmol) in 60 cm3 of tetrahydrofuran are introduced into a three-necked, round-bottomed flash equipped with a septum and a dropping funnel. The mixture is cooled to -10° C. and then 5.5 g of 97% N,N-diethylacetoacetamide (34.0 mmol) are slowly added. The mixture is stirred for 15 minutes. 21.25 cm3 of n-butyllithium in solution in hexane at 1.6 mol/liter are then slowly added and the mixture is then stirred for 15 minutes. 3.05 g of benzaldehyde (28.5 mmol) are introduced. The mixture is stirred for 25 minutes and then 6 cm3 of concentrated hydrochloric acid and 35 cm3 of water are added. Extraction is carried out with 3 times 25 cm3 of dichloromethane. The combined organic phases are washed with 2 times 100 cm3 of water and dried over sodium sulphate. After filtration and concentration to dryness under reduced pressure, there is obtained, with a yield of 97.7%, 7.33 g of N,N-diethyl -5-phenyl-5-hydroxy-3-oxopentanamide, 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 2 times 100 cm3 of water
  6. dry with materialdried over sodium sulphate
  7. filtrationAfter filtration and concentration to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-21ed734c48a043b39f59a427eaeb24c8
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05347039

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