反应详情

温度

0 °C

Ethyl 3-(2-fluorophenyl)-3-oxopropanoate (1.00 g, 4.76 mmol) was dissolved in acetonitrile (14 mL) and treated with triethylamine (0.760 ml, 5.47 mmol, 1.15 equiv). The mixture was cooled to 0° C., treated with 4-acetamidobenzenesulfonylazide (1.26 g, 5.23 mmol, 1.1 equiv) and warmed to ambient temperature over 1.5 hours. The mixture was partially concentrated in vacuo, cooled to 0° C., treated with sodium hydroxide (50 mL, 1 N aqueous) and extracted with chloroform (3×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel gradient chromatography (100:0 to 85:15; hexanes:ethyl acetate) providing the titled compound as a yellow oil.

1. temperaturewarmed to ambient temperature over 1.5 hours
2. concentrationThe mixture was partially concentrated in vacuo
3. temperaturecooled to 0° C.
4. additiontreated with sodium hydroxide (50 mL, 1 N aqueous)
5. extractionextracted with chloroform (3×50 mL)
6. dry with materialThe combined organic extracts were dried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified via silica gel gradient chromatography (100:0 to 85:15; hexanes:ethyl acetate)