2-Pyrrolidone → 1-Phenoxycarbonyl-2-oxopyrrolidine

HRID 892729Notes

Reaction equation

HRID 892729 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11]>C1COCC1>[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11]

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 15891Phenyl chloroformateHCID 24758Sodium hydride

Product 1

HCID 144410901-Phenoxycarbonyl-2-oxopyrrolidineYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

To a solution of 7.36 g (184 mmol) of NaH (60%) in 200 ml of THF was added 15.68 g (184 mmol) of 2-oxopyrrolidine with stirring under ice-cooling, and further the mixture was stirred at room temperature for 1 hr. until H2 gas ceased to evolve. The reaction solution was added to a solution of 29.7 g (190 mmol) of phenyl chloroformate in 100 ml of THF cooled at -60° C. and then stirred at room temperature for 4 hr. The reaction solution was poured into ice water, and then extracted with ethyl acetate. After drying, the solvent was removed by evaporation. When the crystalline residue was recrystallized from CH2Cl2 -ether, 37.8 g of the objective compound (II) melting at 120.0°-121.5° C. was obtained as crystals. Yield: 84.0%.

Workup

  1. temperaturecooling
  2. stirringfurther the mixture was stirred at room temperature for 1 hr
  3. stirringstirred at room temperature for 4 hr
  4. extractionextracted with ethyl acetate
  5. customAfter drying
  6. customthe solvent was removed by evaporation
  7. customWhen the crystalline residue was recrystallized from CH2Cl2 -ether

Sources & evidence

ORD record
ord-d7194c0702814ec6ad470a2f12b04993
Source dataset
uspto-grants-1992_06
Patent number
US05120733

Reaction notes

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