Phenyl chloroformate → 1-Phenoxycarbonyl-2-oxopyrrolidine

HRID 847218Notes

Reaction equation

HRID 847218 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].C[Si](C)(C)[N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18]>C1(C)C=CC=CC=1>[O:4]([C:2]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 844611-(Trimethylsilyl)pyrrolidin-2-one

Product 1

HCID 144410901-Phenoxycarbonyl-2-oxopyrrolidineYield 57.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of phenyl chloroformate (3.13 g, 20.0 mmol) in anhydrous toluene (10 ml) was added a solution of 1-trimethylsilyl-2-pyrrolidinone (3.46 g, 22.0 mmol) in anhydrous toluene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to dryness to give a solid material. Recrystallization from ethanol afforded 2.37 g of colorless prisms. Yield 57.7%.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure to dryness
  2. customto give a solid material
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-759737d89fb548dc9d1d66d2608d8c87
Source dataset
uspto-grants-1992_08
Patent number
US05140041

Reaction notes

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