Water → 4-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-one

HRID 486296Notes

Reaction equation

HRID 486296 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:21][C:22](=O)[CH2:23][CH3:24])[C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[O-]CC.[Na+].O>C(O)C>[CH2:23]([C:22]1[CH2:21][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)[C:11](=[O:20])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 11783283N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamide

Product 1

HCID 117275204-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-oneYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

7.61 g (21.3 mmol) of N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamide synthesized in Example 2 or 3 were dissolved in 35 ml of ethanol, and 0.1 ml of an ethanol solution containing 30% of sodium ethoxide was added at room temperature with stirring. The solution was successively stirred at the same temperature for 2 hours, and the resultant reaction mixture was poured into water, followed by extraction with ethyl acetate. The solvent was distilled off under reduced pressure, and the solution was then purified through silica gel column chromatography (an eluent: hexane/ethyl acetate=4/1) to obtain 5.9 g of the desired product in an oily state (yield: 77.5%).

Workup

  1. additionwas added at room temperature
  2. stirringThe solution was successively stirred at the same temperature for 2 hours
  3. customthe resultant reaction mixture
  4. extractionfollowed by extraction with ethyl acetate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe solution was then purified through silica gel column chromatography (an eluent

Sources & evidence

ORD record
ord-3eca28c9854a4c39a38f61aa765fbd0e
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

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