Реакция #302949

Уравнение реакции

4-iodopyrazole

n-butyllithium

ethyl picolinate

→

titled compound

Выход 10.1%

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

Выход 10.1%

Растворители

ammonium chloride

tetrahydrofuran

hexane

Условия реакции

Обработка

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

Методика

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.

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