反应详情

Combine (S)-4-benzyl-2-oxazolidinone (22.9 g, 129 mmol) and tetrahydrofuran (120 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of n-butyl lithium (52 mL, 2.5 M, 130 mmol). After 15 minutes, slowly add a solution of 4-fluorophenylacetyl chloride (22.3 g, 129 mmol) in tetrahydrofuran (50 mL). Warm to ambient temperature. After 2 hours, quench the reaction mixture by the addition of a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the aqueous layer with diethyl ether. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting wit 15% ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from diethyl ether/hexane to give (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone.

1. temperatureCool in a dry-ice/acetone bath
2. waitAfter 2 hours
3. customquench the reaction mixture
4. additionby the addition of a saturated aqueous sodium bicarbonate solution
5. customSeparate the layers
6. extractionextract the aqueous layer with diethyl ether
7. dry with materialdry over Na2SO4
8. filtrationfilter
9. customevaporate in vacuo
10. customto give a residue
11. additioncontaining fractions
12. customevaporate