Catechol → HCID 71736089, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 3a (500 mg, 2.7 mmol), K2CO3 (750 mg, 5.4 mmol), KI (90 mg, 0.54 mmol) in DMF (50 mL) was bubbled with argon for 10 min Catechol (600 mg, 5.4 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 dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with CH2Cl2 to provide the compound 19 (400 mg, 1.55 mmol, 57%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.86 (s, 1H), 7.15 (t, J=8 Hz, 2H), 6.90 (d, J=8 Hz, 1H), 6.78 (m, 5H), 6.57 (t, J=7.2 Hz, 1H), 4.07 (t, J=6.0 Hz, 2H), 3.68 (t, J=6.0 Hz, 2H), 3.45 (q, J=6.8 Hz, 2H), 1.10 (t, J=6.8 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 148.00, 146.35, 145.81, 129.47, 122.24, 120.06, 117.24, 115.04, 112.86, 67.44, 49.79, 45.65, 12.19; HRMS (ESI, positive) m/z calcd. for C16H20NO2 [M+H]+: 258.1494, found: 258.1465; calcd. for C16H19NO2Na [M+Na]+: 280.1313, found: 280.1345.

Provenance & Evidence