反应详情

温度

-20 °C

To a mixture of tert-butyl N-but-3-enylcarbamate (3.16 g, 18.42 mmol, 1.30 Eq) in THF (20 mL), was added n-BuLi (2.5 M, 14.74 mL, 2.60 Eq) at −78° C. under N2. The mixture was stirred at −20° C. for 1 hr. Then 1-chloro-3-(triphenyl phosphoranylidene)propan-2-one (5.00 g, 14.17 mmol, 1.00 Eq) in THF (20 mL) was added to the mixture at −78° C. under N2. The mixture was stirred at −20° C. for 3 hr. The resulting mixture was poured into water (30 mL) and stirred for 20 min. The aqueous phase was extracted with EA (10 mL). The combined organic phase was washed with saturated brine (20 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (PE/EA=1/1) to afford tert-butyl but-3-en-1-yl(2-oxo-3-(triphenylphosphoranylidene)propyl)carbamate (5.80 g, 11.90 mmol, 83.98% yield) as yellow solid.

1. stirringThe mixture was stirred at −20° C. for 3 hr
2. stirringstirred for 20 min
3. extractionThe aqueous phase was extracted with EA (10 mL)
4. washThe combined organic phase was washed with saturated brine (20 mL*2)
5. dry with materialdried with anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuum
8. customThe residue was purified by silica gel chromatography (PE/EA=1/1)