Diethyl Ether → Ethyl 2-benzylideneamino-2-ethylhexanoate

HRID 342861

Reaction equation

HRID 342861 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

HCID 10107458Ethyl 2-benzylideneamino-2-ethylhexanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (32.49 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) (178.13 g) in DMF was added dropwise. After 2 hours stirring at room temperature, a solution of butyl iodide (149.48 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).

Workup

  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

Sources & evidence

ORD record
ord-5a84ca2a8c5347bd9556224111a9eb8f
Source dataset
uspto-grants-1999_01
Patent number
US05859240

Linked notes

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