Acetyl chloride → 2,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl acetate

HRID 918995Notes

Reaction equation

HRID 918995 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:13])[NH:10][C:9](=[O:11])[CH2:8][C:7]1=[O:12].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:12][C:7]1[C:6]([CH3:13])([CH3:5])[NH:10][C:9](=[O:11])[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 133467095,5-Dimethylpyrrolidine-2,4-dione

Product 1

HCID 704964622,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl acetateYield 18.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

At 0 to 5° C., a solution of 4.08 g of acetyl chloride in 20 of methylene chloride is added dropwise to a solution of 6.36 g of 5,5-dimethylpyrrolidine-2,4-dione and 5.57 g of triethylamine in 50 ml of methylene chloride. The mixture is then left to reach room temperature over the course of approximately one hour and then stirred for a further 24 hours. The reaction mixture is then diluted with 50 ml of methylene chloride, and extracted by shaking twice with in each case 50 ml of water, twice with in each case 25 ml of 5% strength sodium hydroxide solution and once with 50 ml of saturated aqueous NaCl solution. Drying and concentration by evaporation gives 1.58 g of the title compound in a purity according to HPLC of 97%.

Workup

  1. waitThe mixture is then left
  2. customto reach room temperature over the course of approximately one hour
  3. extractionextracted
  4. stirringby shaking twice with in each case 50 ml of water, twice with in each case 25 ml of 5% strength sodium hydroxide solution and once with 50 ml of saturated aqueous NaCl solution
  5. customDrying
  6. concentrationconcentration
  7. customby evaporation

Sources & evidence

ORD record
ord-6ec78d09aa7e44c88e16aef611225546
Source dataset
uspto-grants-2016_03
Patent number
US09272997B2

Reaction notes

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