Hydroquinone → HCID 71736092, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 27a (470 mg, 1.48 mmol), K2CO3 (440 mg, 3 mmol), and KI (50 mg, 0.3 mmol) in DMF (50 mL) was bubbled with argon for 10 min. Hydroquinone (660 mg, 6 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, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide the compound 27 (150 mg, 0.32 mmol, 22% yield) as a brown oil. 1H NMR (CDCl3, 400 MHz) δ 7.05 (d, J=8.4 Hz, 2H), 6.67-6.81 (m, 9H), 5.58 (bs, 2H), 4.09 (t, J=6.4 Hz, 4H), 3.80 (t, J=6.0 Hz, 7H), 3.69 (s, 3H), 2.56 (t, J=7.2 Hz, 2H), 2.35 (t, J=7.2 Hz, 2H), 1.89-1.96 (m, 2H); HRMS (ESI, positive) m/z calcd. for C27H32NO6 [M+H]+: 466.2230, found: 466.2204.

Provenance & Evidence