Allyl iodide → HCID 22414817, compound

Participants

Reaction Conditions

Reaction Steps

8.21 g (42.99 mmol) of 2,3-dihydro-4-hydroxy-3,3,7-trimethyl-1H-indol-2-one and 7.95 g (47.3 mmol) of allyl iodide were dissolved in 65 ml of N,N-dimethylformamide. After the addition of 12.0 g (87 mmol) of potassium carbonate, the mixture was stirred for 2 hours over a water bath at 70° C. After the reaction, the solvent was removed by evaporation under reduced pressure. Chloroform was added to the residue, and the mixture was washed with water, 2N sodium hydroxide aqueous solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 10:1 mixture of chloroform and ethyl acetate) and crystallized from n-hexane to obtain 5.67 g (yield, 57.1%) of colorless crystals of the title compound.

Provenance & Evidence