Ethanol → 3-Hydroxy-1-(4-methoxybenzoyl)pyrrolidin-2-one

HRID 1462939Notes

Reaction equation

HRID 1462939 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]2[CH2:13][CH2:12][C@H:11]([C@@H](Cl)C([O-])=O)[C:10]2=[O:19])=[O:8])=[CH:5][CH:4]=1.NC(N)=S.C([OH:28])C>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]2[C:10](=[O:19])[CH:11]([OH:28])[CH2:12][CH2:13]2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 131713591HCID 131713591, compound

Product 1

HCID 30608043-Hydroxy-1-(4-methoxybenzoyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.54 g of (R,S)-1-(p-methoxybenzoyl)-2-oxo-3-pyrrolidinylchloroacetate are heated at 100° C. in 50 ml of pyridine for 10 minutes under nitrogen with 0.42 g of thiourea and 7 ml of ethanol. The solvent is removed by evaporation and the residue is partitioned between ethyl acetate and water. The organic phase is washed several times with water and the aqueous phases are extracted with ethyl acetate. The combined ethyl acetate phases are evaporated, the residue is boiled at reflux in diisopropyl ether and then the solution is decanted off from insoluble constituents. The clear, colourless diisopropyl ether phase is stirred in an ice-bath and then left to stand in an ice box overnight. The product which crystallises out is filtered off and there is obtained (R,S)-1-(p-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone of melting point 125°-126° C.

Workup

  1. customThe solvent is removed by evaporation
  2. customthe residue is partitioned between ethyl acetate and water
  3. washThe organic phase is washed several times with water
  4. extractionthe aqueous phases are extracted with ethyl acetate
  5. customThe combined ethyl acetate phases are evaporated
  6. temperatureat reflux in diisopropyl ether
  7. customthe solution is decanted off from insoluble constituents
  8. waitleft
  9. customThe product which crystallises out
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-e0538095cc494121a351d18720605888
Source dataset
uspto-grants-1984_07
Patent number
US04461906

Reaction notes

Loading…