反应 #470449

反应方程式

chlorotriisopropylsilane

n-BuLi

pyrrole

N2

→

1-(triisopropylsilyl)-1H-pyrrole

收率 110.1%

溶剂

water

THF

THF

反应条件

后处理

1. 1
   温度The mixture was cooled again to −78° C.
2. 2
   workup.STIRRINGwith stirring
3. 3
   温度Then the mixture was warmed to room temperature
4. 4
   workup.STIRRINGstirred for additional 30 min.
5. 5
   萃取extracted with ether (200 mL)
6. 6
   洗涤The organic layer was washed with water (2×100 mL) and brine (100 mL)
7. 7
   干燥dried over Na2SO4
8. 8
   浓缩concentrated

实验过程

A solution n-BuLi in THF (2.5 M, 19.6 mL, 49 mmol) was added to a stirred solution of pyrrole (3 g, 44.7 mmol) in anhydrous THF (20 mL) at −78° C. in an N2 atmosphere. Then the mixture was warmed to room temperature and stirred at this temperature for 10 min. The mixture was cooled again to −78° C., and chlorotriisopropylsilane (10.5 g, 44.7mmol) was added dropwisely with stirring. Then the mixture was warmed to room temperature and stirred for additional 30 min., diluted with water (200 mL), extracted with ether (200 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), dried over Na2SO4, concentrated to give crude 1-(triisopropylsilyl)-1H-pyrrole (11 g, 100%) as a oil. LCMS: 224 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 0.98 (m, 18H), 1.40 (m 3H), 6.20 (m, 2H), 6.80 (m, 2H).

来源