Reaktion #302949

Reaktionsgleichung

4-iodopyrazole

n-butyllithium

ethyl picolinate

→

titled compound

Ausbeute 10.1%

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

Ausbeute 10.1%

Lösungsmittel

ammonium chloride

tetrahydrofuran

hexane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle