2-(8-Iodooctyl)-4,5,6,7-tetramethoxyindan → HCID 18348600, compound

HRID 2268475

Reaction equation

HRID 2268475 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[C:13]([O:25][CH3:26])[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]=2[O:19][CH3:20])[CH2:11]1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K]>CN(C=O)C.C(OCC)(=O)C>[CH3:26][O:25][C:13]1[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]([O:19][CH3:20])=[C:17]2[C:12]=1[CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:31]1[C:30](=[O:32])[C:29]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]3[C:27]1=[O:37])[CH2:18]2

Participants

5

Reactant 2

HCID 183485412-(8-Iodooctyl)-4,5,6,7-tetramethoxyindanHCID 24194345Phthalimide potassium salt

Product 1

HCID 18348600HCID 18348600, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(8-iodooctyl)-4,5,6,7-tetramethoxyindan (1.98 g) in DMF (10 ml) was dropwise added potassium phthalimide (924 mg). After being stirred at room temperature for 12 hr, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo and the residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=10:1) and then recrystallized from hexane gave the entitled compound (1.74 g) as crystals.

Workup

  1. washThe organic layer was washed with water and saturated aqueous sodium chloride
  2. customdried
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=10:1)
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-27ca368188ec4fc688f41f82c13cf516
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Linked notes

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