反应详情

To a stirring solution of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (100 mg, 0.4 mmol) in DMSO (2 ml), potassium tert-butoxide (106 mg, 0.941 mmol) was added. Stirring continued at RT for about 1 hour. 2-Bromo-3′-methoxyacetophenone (100 mg, 0.5 mmol) was then added to the mixture. After 2 hours, LCMS showed that the reaction was complete. The reaction mixture was partitioned between EtOAc and water, and the aqueous phase was extracted with EtOAc. Combined extracts were washed with brine, dried on (Na2SO4), filtered, and evaporated in vacuo. The residue was analyzed on a small RediSep column eluting with 0-10% acetone/DCM. Fractions containing the product were combined and evaporated in vacuo to afford 70 mg of 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione as a pale yellow solid.

1. waitAfter 2 hours
2. customThe reaction mixture was partitioned between EtOAc and water
3. extractionthe aqueous phase was extracted with EtOAc
4. washCombined extracts were washed with brine
5. dry with materialdried on (Na2SO4)
6. filtrationfiltered
7. customevaporated in vacuo
8. washeluting with 0-10% acetone/DCM
9. additionFractions containing the product
10. customevaporated in vacuo