Phthalimide potassium salt → 2-[4-(3,3-Dimethyl-butyryl)-benzyl]-isoindole-1,3-dione

HRID 911586Notes

Reaction equation

HRID 911586 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)=[O:5].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][N:20]2[C:16](=[O:26])[C:17]3[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19]2=[O:21])=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 57656172HCID 57656172, compound

Product 1

HCID 576560342-[4-(3,3-Dimethyl-butyryl)-benzyl]-isoindole-1,3-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 4-(3,3-dimethyl-butyryl)-benzyl bromide (1 g, 3.731 mmol) to a stirred suspension of potassium phthalimide (0.705 g, 3.805 mmol) in anhydrous DMF (20 mL). Stir the mixture overnight at room temperature. Dilute with EtOAc and wash twice with ice-cold water. Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (19:1, 4:1) to provide the desired intermediate as oil (1.24 g, 100%).

Workup

  1. washwash twice with ice-cold water
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (19:1, 4:1)

Sources & evidence

ORD record
ord-59dc6b84e83c4b659cc8627f374efe5e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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