Iodine → HCID 86752693, compound

Participants

Reaction Steps

Iodine (657 mg, 2.59 mmol) was dissolved in 5 mL of THF and the solution was added to a solution of 2-(2-(trimethylsilyl)ethenyl)-4,4-dimethyl-2-cyclohexen-1-one (Compound 18, 575 mg, 2.59 mmol) and dichloromethane (15 mL) at room temperature. The solution was stirred for 6 hours, and then treated with 10% aqueous Na2S2O3 to remove the excess iodine. The layers were separated and the aqueous layer was extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate) to give the product as a brown oil.

Provenance & Evidence