反应详情

Combine (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone (14.28 g, 45.6 mmol) and tetrahydrofuran (150 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of sodium bis(trimethylsilyl)amide (50 mL, 1.0 M in tetrahydrofuran, 50 mmol). After 25 minutes, add allyl iodide (13 mL, 142.2 mmol) and then replace the bath with a dry-ice/carbon tetrachloride bath. After 1 hour, quench the reaction by the addition of a saturated aqueous ammonium chloride solution, extract with diethyl ether, and separate the layers. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/6 ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from chloroform/hexane to give (S)-4-benzyl-3-(2-(4-fluorophenyl)pent-4-enoyl)-2-oxazolidinone: mp; 103-104° C. Rf=0.57 (silica gel, 20% ethyl acetate/hexane).

1. temperatureCool in a dry-ice/acetone bath
2. waitAfter 1 hour
3. customquench
4. customthe reaction
5. extractionextract with diethyl ether
6. customseparate the layers
7. dry with materialDry the organic layer over Na2SO4
8. filtrationfilter
9. customevaporate in vacuo
10. customto give a residue
11. additioncontaining fractions
12. customevaporate