反应详情

A mixture of 4-bromo-2-methoxy-phenol (50.8 mg, 0.25 mmol), 2-(4-methyl-thiazol-5-yl)-ethanol (49.5 mg, 0.25 mmol) and polymer-supported triphenyl phosphine (250 mg, 0.75 mmol) in THF (2.5 mL) was stirred at room temperature for 20 minutes. DBAD (86.3 mg, 0.375 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was filtered through Celite®, rinsing with THF and methanol. The filtrate was concentrated, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel (10 to 20% ethyl acetate in hexane) to give the title compound. MS (ESI) m/e 329 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 8.82 (s, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.03 (dd, J=8.5, 2.4 Hz, 1H), 6.91 (d, J=8.5 Hz, 1H), 4.10 (t, J=6.4 Hz, 2H), 3.77 (s, 3H), 3.20 (t, J=6.4 Hz, 2H), 2.35 (s, 3H).

1. stirringthe mixture was stirred overnight at room temperature
2. filtrationThe reaction mixture was filtered through Celite®
3. washrinsing with THF and methanol
4. concentrationThe filtrate was concentrated
5. additiondiluted with ethyl acetate
6. washwashed with water and brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe concentrate was purified by column chromatography on silica gel (10 to 20% ethyl acetate in hexane)