Sodium Chloride → 5-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

HRID 594397Notes

Reaction equation

HRID 594397 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[CH:15](C(OCC)=O)[C:14](=[O:21])[C:13](=[O:22])[N:12]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1.[Na+].[Cl-]>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:12]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=2)[C:13](=[O:22])[C:14](=[O:21])[CH2:15]1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 69082391Ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate

Product 1

HCID 690846265-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A mixture of ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate (11.400 g; 23.68 mmol) and NaCl (2.767 g; 47.36 mmol) in DMSO (111 ml) and water (37 ml) was refluxed, under nitrogen, for 3 h. After cooling to rt, water (150 ml) was added, and the mixture was extracted with AcOEt (3×150 ml). The mixed organic layers were washed with brine (50 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Addition of Et2O and trituration allowed the precipitation of the product. Subsequent filtration, and drying of the obtained solid under HV afforded 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione as a pink solid. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 410.15 g/mol.

Workup

  1. temperaturewas refluxed, under nitrogen, for 3 h
  2. extractionthe mixture was extracted with AcOEt (3×150 ml)
  3. washThe mixed organic layers were washed with brine (50 ml)
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionAddition of Et2O and trituration
  8. customthe precipitation of the product
  9. filtrationSubsequent filtration
  10. customdrying of the obtained solid under HV

Sources & evidence

ORD record
ord-8e1d897773b54a5eb88f0126f915acbc
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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