反应详情

温度

0 °C

To a stirring solution of 5-{4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.62 g, 1.7 mmol) in DCM (15 mL) was added DMSO (0.5 mL) and the solution was cooled to 0° C. Added phosphorus pentoxide (0.52 g, 1.8 mmol) followed by triethylamine (1.2 mL, 8.3 mmol). The reaction was allowed to slowly warm to RT. After 2 hours water was added and the phases were separated. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH. The aqueous phase was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.33 g (54%) of the title compound as a white solid. MS (ESI+) for C19H17NO5S m/z 372.0 (M+H)+. MS (ESI−) for C19H17NO5S m/z 370.1 (M−H)−.

1. temperatureto slowly warm to RT
2. customthe phases were separated
3. extractionThe aqueous phase was extracted with EtOAc
4. washThe combined extracts were washed with brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe resulting white solid was chromatographed on a small silica gel column
9. washeluting with 10% EtOAc/DCM
10. additionFractions containing product
11. customevaporated in vacuo