反应详情

To acetone (225 mL) was added ({2-[hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl ester (4.17 g, 8.35 mmol), and 8N Jones reagent (4 mL). The mixture was stirred 15 minutes giving a suspended solid. Isopropanol (20 mL) was added followed by stirring for 15 minutes. The mixture was filtered, saturated sodium bicarbonate solution was added, and the solvent was removed in vacuo giving a paste. The paste was resuspended in ethyl acetate and water, filtered, and washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. The solution was filtered and evaporated to a solid which was crystallized from ethyl acetate and ethyl ether giving a white solid, 2.41 g, 59% yield, mp 159-170° C. NMR spectra and elemental analysis were consistent with the structure.

1. customgiving a suspended solid
2. stirringby stirring for 15 minutes
3. filtrationThe mixture was filtered
4. additionsaturated sodium bicarbonate solution was added
5. customthe solvent was removed in vacuo
6. customgiving a paste
7. filtrationwater, filtered
8. washwashed with saturated sodium bicarbonate, brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationThe solution was filtered
11. customevaporated to a solid which
12. customwas crystallized from ethyl acetate and ethyl ether giving a white solid, 2.41 g, 59% yield, mp 159-170° C