Reacción #302949

Ecuación de reacción

4-iodopyrazole

n-butyllithium

ethyl picolinate

→

titled compound

Rendimiento 10.1%

(1H-pyrazol-4-yl)-pyridin-2-ylmethanone

Rendimiento 10.1%

Disolventes

ammonium chloride

tetrahydrofuran

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to −10° C.
2. 2
   workup.STIRRINGby stirring at room temperature for 1.5 hours
3. 3
   Extracciónextracted with diethyl ether
4. 4
   LavadoThe organic layer was washed with brine
5. 5
   Secadodried over sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1 to 1:2)

Procedimiento

To a solution of 4-iodopyrazole (1.0 g) in tetrahydrofuran (10 mL), a solution of n-butyllithium in hexane (2.6 M, 4.8 mL) was added dropwise at −10° C. and stirred at room temperature for 1 hour. The reaction mixture was cooled to −10° C. and ethyl picolinate (0.86 g) was added thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with saturated aqueous ammonium chloride and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1 to 1:2) to give the titled compound (0.090 g) as a colorless solid.

Fuente