Reacción #57360

Ecuación de reacción

2,6-dibromopyridine

BuLi

4,4,N-Trimethoxy-N-methyl-butyramide

→

N-[1-Eth-(Z)-ylidene-5,5-dimethoxy-2-oxo-pentyl]-acrylimidoyl bromide

Rendimiento 74.9%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring at −70° C. for 1.5 hr
2. 2
   Otrothe reaction mixture is quenched with 120 mL of water
3. 3
   Extracciónextracted with 3×130 mL of EtOAc
4. 4
   ConcentraciónThe combined organic layers is concentrated
5. 5
   Otropurified by chromatography(Hexane/EtOAc:70/30)

Procedimiento

To a suspension of 2,6-dibromopyridine(8.1 g, 34.03 mmol) in 80 mL of ether at −70° C., is added BuLi(12.3 mL, 26.17 mmol, 2.5 M in Hexane) in on portion. After stirring at −70° C. for 5 min, 4,4,N-Trimethoxy-N-methyl-butyramide(5.0 g, 26.17 mmol) is added to the solution dropwise. After stirring at −70° C. for 1.5 hr, the reaction mixture is quenched with 120 mL of water and extracted with 3×130 mL of EtOAc. The combined organic layers is concentrated and purified by chromatography(Hexane/EtOAc:70/30) to give N-[1-Eth-(Z)-ylidene-5,5-dimethoxy-2-oxo-pentyl]-acrylimidoyl bromide(5.96 g, 60.5%) as light yellow liquid. M/Z=288.0

Fuente