反应详情

A mixture of 3-(5-amino-1,3,4-thiadiazol-2-yl)pentan-3-ol (0.129 g, 0.689 mmol), 4-(4-fluorophenyl)-2-oxo-2H-chromene-7-carbaldehyde (0.200 g, 0.746 mmol) and acetic acid (7.94 μL, 0.138 mmol) in benzene (2.5 mL) was stirred overnight at reflux with a Dean-Stark trap. After cooling, the mixture was diluted in THF (5 mL) and sodium triacetoxyborohydride (0.731 g, 3.45 mmol) was added. The mixture was then stirred at 45° C. for 3 h. The reaction was quenched with a saturated NaHCO3 solution and portioned between EtOAc and water. The organic layer was dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (Hexane-EtOAc-MeOH, 50:50:0 to 0:98:2) to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.7 (m, 2H), 7.5 (s, 1H), 7.45 (s, 1H), 7.4 (m, 3H), 6.35 (s, 1H), 4.75 (s, 2H), 4.5 (bs, 1H), 2.0-1.75 (m, 4H), 0.9 (t, 6H).

1. temperatureat reflux with a Dean-Stark trap
2. temperatureAfter cooling
3. stirringThe mixture was then stirred at 45° C. for 3 h
4. customThe reaction was quenched with a saturated NaHCO3 solution
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude residue obtained
9. customwas purified by column chromatography (Hexane-EtOAc-MeOH, 50:50:0 to 0:98:2)