反应详情

Sodium metal (23 mg, 1 mmol) was added to 25 mL of methanol. After the sodium metal was consumed, methyl acetoacetate (1.16 g, 10 mmol) was added to the mixture and stirred for 15 minutes. A solution of phenyl vinyl sulfone (1.68 g, 10 mmol) was added dropwise to the solution and maintained for several hours. The slightly yellow solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford a clear oil. The material was purified via flash column chromatography on silica gel (eluting with hexane:ethyl acetate in a gradient from 3:2 to 2:3) to afford 1.40 g of ethyl 2-(2-benzenesulfonylethyl)-3-oxo-butyrate.

1. customAfter the sodium metal was consumed
2. temperaturemaintained for several hours
3. concentrationThe slightly yellow solution was concentrated under reduced pressure
4. additionthe residue was diluted with ethyl acetate
5. washwashed with saturated aqueous ammonium chloride
6. extractionThe aqueous layer was extracted with ethyl acetate
7. washthe combined organic layers were washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customto afford a clear oil
12. customThe material was purified via flash column chromatography on silica gel (
13. washeluting with hexane