Reacción #167702

Ecuación de reacción

I2

nicotinonitrile

2,2,6,6-tetramethyl-piperidine

butyllithium

→

title compound

4-iodo-nicotinonitrile

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas slowly added
2. 2
   workup.STIRRINGAfter stirring for 2 hours
3. 3
   Otrothe mixture was quenched with 500 mL of ice-water
4. 4
   OtroTetrahydrofuran was removed under reduced pressure
5. 5
   Extracciónthe aqueous phase was extracted with ether
6. 6
   LavadoThe organic phase was washed with brine, citric acid, brine, aqueous Na2S2O3 and brine again
7. 7
   SecadoAfter being dried over Na2SO4
8. 8
   Concentraciónthe organic phase was concentrated
9. 9
   Otropurified

Procedimiento

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.

Fuente