Iodine → HCID 22414832, compound

Participants

Reaction Steps

287 mg (1.13 mmol) of iodine was dissolved in a 4:1 chloroform-methanol solvent. To the solution were added 191 mg of potassium iodide and 4:1 chloroform-methanol solvent, followed by stirring to homogenize. This potassium iodide solution in 4:1 chloroform-methanol was added to a 4:1 chloroform-methanol solution of 259 mg (1 mmol) of 2,3-dihydro-4-hydroxy-5-(1-methyl-2-butenyl)-3,3,7-trimethyl-1H-indol-2-one under an argon atmosphere, and the mixture was stirred for 15 hours at room temperature. After the addition of an aqueous solution of sodium hydrogen sulfite, the reaction mixture was extracted with chloroform. The extract was washed with 1N sodium hydroxide solution and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by separation thin layer chromatography (silica gel, 2:1 mixture of n-hexane and ethyl acetate) to obtain, as a low polarity component, 122 mg (yield 31.7%) of light yellow crystals of the title compound (a).

Provenance & Evidence