Water → 107259-14-3

HRID 1198608Notes

Reaction equation

HRID 1198608 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13](=[O:18])[CH2:14]C([O-])=O)[CH2:10][C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Na+].O>CS(C)=O>[C:13]([CH:11]1[CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:19])[CH2:10]1)(=[O:18])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 19102755HCID 19102755, compound

Product 1

HCID 10082072107259-14-3Yield 83.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-(1-benzyl-2-oxopyrrolidin-4-yl)-3-oxopropanoate (24.0 g, 0.083 mole) and sodium chloride (10.6 g, 0.181 mole) in dimethylsulfoxide (105 mL)/water (4.4 mL) was heated at 135° with stirring for 16 hours. On cooling the reaction mixture was poured onto ice water (900 mL) and extracted with dichloromethane (800 mL). The organic phase was washed with water (4×500 mL) and dried (MgSO4). The solvent was removed under reduced pressure to give 4-acetyl-1-benzyl-2-pyrrolidinone (15.0 g, 83%) as a brown oil.

Workup

  1. temperaturewas heated at 135°
  2. temperatureOn cooling the reaction mixture
  3. additionwas poured onto ice water (900 mL)
  4. extractionextracted with dichloromethane (800 mL)
  5. washThe organic phase was washed with water (4×500 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fb770d900b0e4b18ad802b5fc0f1a253
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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