反応 #167702

反応方程式

I2

nicotinonitrile

2,2,6,6-tetramethyl-piperidine

butyllithium

→

title compound

4-iodo-nicotinonitrile

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas slowly added
2. 2
   workup.STIRRINGAfter stirring for 2 hours
3. 3
   その他the mixture was quenched with 500 mL of ice-water
4. 4
   その他Tetrahydrofuran was removed under reduced pressure
5. 5
   抽出the aqueous phase was extracted with ether
6. 6
   洗浄The organic phase was washed with brine, citric acid, brine, aqueous Na2S2O3 and brine again
7. 7
   乾燥After being dried over Na2SO4
8. 8
   濃縮the organic phase was concentrated
9. 9
   その他purified

実験手順

To a stirred solution of 2,2,6,6-tetramethyl-piperidine (42.3 g, 0.3 mol) in 2 L of tetrahydrofuran was added butyllithium (120 mL, 2.5M, 0.3 mol) at −78° C. under N2 atmosphere. The mixture was stirred for 1 hour before a solution of nicotinonitrile (26 g, 0.25 mol) in 500 mL of tetrahydrofuran was slowly added, and the resulting mixture was stirred for 0.5 hour at −78° C. Then I2 (76.2 g, 0.3 mol) in 500 mL of tetrahydrofuran was added in a dropwise manner. After stirring for 2 hours, the mixture was quenched with 500 mL of ice-water. Tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted with ether. The organic phase was washed with brine, citric acid, brine, aqueous Na2S2O3 and brine again. After being dried over Na2SO4, the organic phase was concentrated and purified by using column chromatography on silica gel (petroleum ether:ethyl acetate, 10:1) to obtain the title compound.

出典