Methyl iodide → 2,3-Dihydro-5-methoxy-2,3,3-trimethyl-1H-isoindol-1-one

HRID 2088745Notes

Reaction equation

HRID 2088745 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][C:8]2([CH3:16])[CH3:15].[CH3:17]I>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([CH3:17])[C:8]2([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 105838765-Methoxy-3,3-dimethylisoindolin-1-one

Product 1

HCID 672244622,3-Dihydro-5-methoxy-2,3,3-trimethyl-1H-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With cooling with ice, 96 mg of 60% sodium hydride was added to 8.0 mL of a DMF solution of 382 mg of 5-methoxy-3,3-dimethylisoindolin-1-one, and stirred for 30 minutes with cooling with ice. 0.19 mL of methyl iodide was added to it, and stirred at room temperature for 7 hours. The solvent was evaporated away under reduced pressure, water was added to the residue and extracted with ethyl acetate. The organic layer was washed with water and aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 381 mg of the entitled compound as a colorless solid.

Workup

  1. temperaturewith cooling with ice
  2. stirringstirred at room temperature for 7 hours
  3. customThe solvent was evaporated away under reduced pressure, water
  4. additionwas added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and aqueous saturated sodium chloride solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aef47ed4c8534ee0b583128b38c4d33e
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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