m-Chloroperbenzoic acid → HCID 57830182, compound

HRID 2412213Notes

Reaction equation

HRID 2412213 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 mol) 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 washed with NaOH again. The organic layer 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 washed with NaOH again
  3. washThe organic layer washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe product was filtered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d6c886b9e1af4a4eb764686b4a08faaa
Source dataset
uspto-grants-2014_08
Patent number
US08816087B2

Reaction notes

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