m-Chloroperbenzoic acid → 1-{4-[(Oxiran-2-yl)methoxy]phenyl}-1H-pyrrole-2,5-dione

HRID 1977443Notes

Reaction equation

HRID 1977443 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[CH:14]=[CH:13][C:12]2=[O:17])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:23]>ClCCl>[O:23]1[CH2:3][CH:2]1[CH2:1][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15](=[O:16])[CH:14]=[CH:13][C:12]2=[O:17])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 139068011-{4-[(Prop-2-en-1-yl)oxy]phenyl}-1H-pyrrole-2,5-dione

Product 1

HCID 219980621-{4-[(Oxiran-2-yl)methoxy]phenyl}-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Allyloxyphenyl)maleimide (175 g, 76.4 mole) and 3-chloroperoxybenzoic acid (262 g, 70-75%, Across) were dissolved in 2.0 l of dichloromethane. After stirring for 72 h at room temperature, the reaction mixture was concentrated under reduced pressure to a slurry. Ether (2.0 l) was added to the slurry and stirred for 0.5 h at room temperature. The product was filtered off, washed with ether, and dried in an oven.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure to a slurry
  2. additionEther (2.0 l) was added to the slurry
  3. stirringstirred for 0.5 h at room temperature
  4. filtrationThe product was filtered off
  5. washwashed with ether
  6. customdried in an oven

Sources & evidence

ORD record
ord-b03691d5c32b43289936aaa6f109fb38
Source dataset
uspto-grants-2001_05
Patent number
US06232430B1

Reaction notes

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