Iodoethane → HCID 67538067, compound

Participants

Reaction Steps

To a solution of 1-(4-(difluoromethoxy)phenyl)-2-(3-(4-hydroxybut-1-ynyl)phenyl)ethane-1,2-dione (344 mg, 1.0 mmol) from the previous step in DCM (5 mL) was added tetrabutylammonium bromide (64 mg, 0.2 mmol) followed by NaOH (2.5N, 5 mL). Ethyl iodide (3.9 g, 2.0 mL, 25 mmol) was added and the mixture was stirred vigorously for 2 d then worked up as follows. The reaction mixture was diluted with water and DCM. The aqueous layer was separated and extracted once with DCM. The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to give an oil. Flash chromatography (SiO2, 1:9 EtOAc:Hexanes to 1:1 EtOAc:Hexanes) to provide 100 mg, 26%, of the title compound as a yellow oil.

Provenance & Evidence