m-Chloroperbenzoic acid → 2-[2-(oxiran-2-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1626307

Reaction equation

HRID 1626307 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH:3]=[CH2:4].ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[O:21]1[CH2:4][CH:3]1[CH2:2][CH2:1][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 339432N-(3-Buten-1-yl)phthalimide

Product 1

HCID 3394332-[2-(oxiran-2-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dioneYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(but-3-en-1-yl)isoindoline-1,3-dione obtained in step 1 (0.65 g, 3.22 mmol) in dichloromethane (10 ml), was added m-chloroperoxybenzoic acid (1.11 g, 6.44 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 10 hours. After the reaction complete, the reaction mixture thus obtained was filtered through a plug of Celite. The filtrate was washed with 1 N sodium hydroxide solution and brine. The organic phase thus separated was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.65 g). The compound was used for the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customAfter the reaction complete, the reaction mixture thus obtained
  3. filtrationwas filtered through a plug of Celite
  4. washThe filtrate was washed with 1 N sodium hydroxide solution and brine
  5. customThe organic phase thus separated
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-859ff5f4a9b2419db260b9a33db117c4
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Linked notes

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