m-Chloroperbenzoic acid → HCID 57830182, compound

HRID 41449Notes

Reaction equation

HRID 41449 reaction equation
[CH:1]([C:4]1[C:5]([O:25][CH3:26])=[CH:6][C:7]([O:23][CH3:24])=[C:8]([C:10]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:21]=[CH2:22])[CH:18]=3)[CH2:13]2)=[O:11])[CH:9]=1)([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:35])C=1>C(Cl)Cl.[OH-].[Na+]>[CH:1]([C:4]1[C:5]([O:25][CH3:26])=[CH:6][C:7]([O:23][CH3:24])=[C:8]([C:10]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:21]4[CH2:22][O:35]4)[CH:18]=3)[CH2:13]2)=[O:11])[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59006993HCID 59006993, compound

Product 1

HCID 57830182HCID 57830182, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To (5-isopropyl-2,4-dimethoxy-phenyl)-(5-vinyl-1,3-dihydro-isoindol-2-yl)-methanone (0.80 g, 2.28 mmol) in DCM (22 ml) was added mCPBA (0.61 g, 2.73 mmol) at 0° C. The reaction was stirred at room temperature for an hour. The reaction was diluted with NaOH (1M, aq.) and extracted the product with EtOAc. The EtOAc layer was washed with NaOH again. The organic layer was washed with brine and dried over MgSO4. The product was filtered and evaporated to dryness to yield crude (5-isopropyl-2,4-dimethoxy-phenyl)-(5-oxiranyl-1,3-dihydro-isoindol-2-yl)-methanone as a very pale yellow oil. MS: [M+H]+ 368.

Workup

  1. extractionextracted the product with EtOAc
  2. washThe EtOAc layer was washed with NaOH again
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe product was filtered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-74a2d33a2c504367b52d78497d002847
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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