반응 #1841468

반응 방정식

water

n-BuLi

tert-butyl N-but-3-enylcarbamate

1-chloro-3-(triphenyl phosphoranylidene)propan-2-one

→

tert-butyl but-3-en-1-yl(2-oxo-3-(triphenylphosphoranylidene)propyl)carbamate

수율 84.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at −20° C. for 3 hr
2. 2
   workup.STIRRINGstirred for 20 min
3. 3
   추출The aqueous phase was extracted with EA (10 mL)
4. 4
   세척The combined organic phase was washed with saturated brine (20 mL*2)
5. 5
   건조dried with anhydrous Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuum
8. 8
   기타The residue was purified by silica gel chromatography (PE/EA=1/1)

실험 절차

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.

출처