反应详情

温度

-78 °C

To a solution of 5.50 g (0.017 mol) of the oxazolidinone in 40 mL of THF, cooled to -78 ° C., was added 17.3 mL (0.035 mol) of a 2.0M solution of lithium diisopropylamide in heptane/THF/benzene. The resulting mixture was stirred at -78° C. for 1 h and then neat allyl bromide (7.5 mL, 0.087 mol) was added to the reaction mixture. The reaction was allowed to warm to 0 degrees (ice bath) and stirred for an additional 3 h and then quenched with 5% HCl solution. The resulting mixture was extracted with ether and the combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 5.0 g (81%) of the desired allylated product as a colorless oil. Electrospray Mass Spec: 358.2 (M+H)+.

1. temperatureto warm to 0 degrees (ice bath)
2. stirringstirred for an additional 3 h
3. customquenched with 5% HCl solution
4. extractionThe resulting mixture was extracted with ether
5. washthe combined organic layers were washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)
10. customto provide 5.0 g (81%) of the