Hydroquinone → HCID 21335871, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 1a (338 mg, 2 mmol), K2CO3 (553 mg, 4 mmol), and KI (66 mg, 0.4 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (440 mg, 4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water and then brine and was dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography on silica gel to provide the compound (150 mg, 0.62 mmol, 31% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.32 (br s, 1H), 7.60 (d, J=7.6 Hz, 2H), 7.38 (t, J=7.8 Hz, 2H), 7.18 (t, J=7.4 Hz, 1H), 6.90 (d, J=9.2 Hz, 2H), 6.84 (d, J=9.2 Hz, 2H), 5.07 (br s, 1H), 4.58 (s, 2H).

Provenance & Evidence