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

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Reaction Steps

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.

Provenance & Evidence