Water → 5,6-Dichloro-2-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)isoindoline

HRID 1017835Notes

Reaction equation

HRID 1017835 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[Cl:21])[C:17](=O)[N:16]([C:23]1[C:24]([CH3:42])=[C:25]([CH3:41])[C:26]3[O:30][C:29]([CH3:32])([CH3:31])[CH:28]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]=3[C:39]=1[CH3:40])[C:15]2=O.O>O1CCCC1>[Cl:21][C:20]1[CH:19]=[C:18]2[C:14](=[CH:13][C:12]=1[Cl:11])[CH2:15][N:16]([C:23]1[C:24]([CH3:42])=[C:25]([CH3:41])[C:26]3[O:30][C:29]([CH3:31])([CH3:32])[CH:28]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:27]=3[C:39]=1[CH3:40])[CH2:17]2

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 219613375,6-Dichloro-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 155165595,6-Dichloro-2-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)isoindolineYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aluminum chloride (1.01 g, 7.59 mmol) in tetrahydrofuran (30 ml) was added lithium aluminum hydride (276.5 mg, 7.29 mmol) and the resulting mixture was stirred for 10 minutes. To this mixture was added a solution of 5,6-dichloro-2-[2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione (907.4 mg, 1.89 mmol) in tetrahydrofuran (10 ml) and the resulting mixture was refluxed with heating for 2 hours. The reaction mixture was cooled down to room temperature and water was added into the mixture. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 153 mg (18% yield) of the title compound. Melting point: 194-196° C.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. extractionThe product was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-397d1cd6ad004147a8b777f28dc97705
Source dataset
uspto-grants-2002_11
Patent number
US06479536B1

Reaction notes

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