Diethyl Ether → Ethyl 2-benzylideneamino-2-ethylhexanoate

HRID 398810

Reaktionsgleichung

Reaktionsgleichung von HRID 398810
[H-].[Na+].[CH:3](=[N:10][CH:11]([CH2:17][CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:19](I)[CH2:20]CC.[Cl-].[NH4+].[CH2:26](OCC)[CH3:27]>CN(C)C=O.O>[CH:3](=[N:10][C:11]([CH2:26][CH3:27])([CH2:17][CH2:18][CH2:19][CH3:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

8

Edukt 5

HCID 3283Diethyl EtherHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10331026Ethyl 2-benzylideneaminobutyrate

Produkt 1

HCID 10107458Ethyl 2-benzylideneamino-2-ethylhexanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

Sodium hydride (32.5 g, 60% dispersion in oil) and N,N-dimethylformamide (DMF) (700 ml) were stirred under nitrogen at room temperature and a solution of the product from (b) (178.1 g) in DMF was added dropwise. After 2 hours stirring at room temperature, a solution of butyl iodide (149.5 g) in DMF was added dropwise and the reaction left stirring for a further 2 hours. The reaction was poured into an ice cold mixture of water (560 ml), diethyl ether (300 ml) and ammonium chloride (120 g). The resulting organic layer was dried over potassium carbonate then concentrated to give the desired product as a brown oil (220 g).

Aufarbeitung

  1. waitthe reaction left
  2. stirringstirring for a further 2 hours
  3. dry with materialThe resulting organic layer was dried over potassium carbonate
  4. concentrationthen concentrated

Quellen und Nachweise

ORD-Eintrag
ord-67b80e9de909443fa754ebafe5ec1aa4
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817652

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