反应详情

Alternately, combine (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone (43.08 g, 426 mmol) and tetrahydrofuran (450 ml). Cool in a dry-ice/acetone bath. Add dropwise a solution of sodium bis(trimethylsilyl)amide (153.0 ml, 1 M in tetrahydrofuran, 137.5 mmol). After 40 minutes, add a solution of allyl iodide (39.0 ml, 426 mmol) and replace the bath with a dry-ice/carbon tetrachloride bath. After 1.5 hours, quench the reaction by the addition of a saturated aqueous solution of ammonium chloride, add diethyl ether (200 ml), and stir. After about 30 minutes, separate the layers and extract the aqueous layer twice with diethyl ether. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a residue. Dry the residue in a vacuum, dissolve in ethyl acetate (about 400 ml), and extract with a saturated aqueous sodium thiosulfate solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 13% ethyl acetate/hexane to give (S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone.

1. temperatureCool in a dry-ice/acetone bath
2. waitAfter 1.5 hours
3. customquench
4. customthe reaction
5. waitAfter about 30 minutes
6. customseparate the layers
7. extractionextract the aqueous layer twice with diethyl ether
8. dry with materialDry the combined organic layers over MgSO4
9. filtrationfilter
10. customevaporate in vacuo
11. customto give a residue
12. customDry the residue in a vacuum
13. dissolutiondissolve in ethyl acetate (about 400 ml)
14. extractionextract with a saturated aqueous sodium thiosulfate solution
15. dry with materialDry the organic layer over MgSO4
16. filtrationfilter
17. customevaporate in vacuo
18. customto give a residue