4-Fluorobenzenesulfonyl chloride → 1-(4-Fluorobenzenesulfonyl)-5-methyl-2-pyrrolidinone

HRID 2086917Notes

Reaction equation

HRID 2086917 reaction equation
[CH3:1][CH:2]1[NH:6][C:5](=[O:7])[CH2:4][CH2:3]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C1COCC1.C([O-])(O)=O.[Na+]>[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:6]2[CH:2]([CH3:1])[CH2:3][CH2:4][C:5]2=[O:7])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 660555-Methyl-2-pyrrolidone

Product 1

HCID 227253831-(4-Fluorobenzenesulfonyl)-5-methyl-2-pyrrolidinoneYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A flame dried flask was charged with 444 mg sodium hydride (60% wt in oil, 11.1 mmol, 1.1 equiv) under N2. The solid was washed (2×hexanes) followed by the addition of 100 mL anhydrous THF. The solution was cooled to 0° C. followed by the addition of 1 g 5-methyl-2-pyrrolidinone (10.09 mmol, 1.0 equiv). The solution was allowed to stir for 20 min, followed by the addition of 1.96 g 4-fluorobenzenesulfonyl chloride (10.09 mmol, 1.0 equiv) in 10 mL THF. After stirring for an additional 50 min, the solution was diluted with sat. NaHCO3, and the THF was removed under reduced pressure. The solution was then extracted (3×EtOAc), dried (MgSO4), and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 30% EtOAc/hexanes) gave the product 1-(4-fluorobenzenesulfonyl)-5-methyl-2-pyrrolidinone as a white solid (949 mg, 3.69 mmol, 37%).

Workup

  1. customA flame dried flask
  2. additionwas charged with 444 mg sodium hydride (60% wt in oil, 11.1 mmol, 1.1 equiv) under N2
  3. washThe solid was washed (2×hexanes)
  4. additionfollowed by the addition of 100 mL anhydrous THF
  5. stirringAfter stirring for an additional 50 min
  6. customthe THF was removed under reduced pressure
  7. extractionThe solution was then extracted (3×EtOAc)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash chromatography (SiO2, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-20ad013ce3654b8fa104e9654a6b8105
Source dataset
uspto-grants-2004_04
Patent number
US06727267B2

Reaction notes

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