Reaktion #40706

Reaktionsgleichung

H2O

ethyl 2-chloronicotinate

4-phenylpyrazole

K2CO3

→

oil

Ausbeute 79.8%

Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylate

Ausbeute 79.8%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionafter extraction with ethyl acetate
2. 2
   Waschenthe organic phase was washed with H2O and sat. NaCl solution
3. 3
   SonstigeThe crude product obtained
4. 4
   Sonstigeafter drying
5. 5
   Sonstigeconcentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%)

Vorschrift

A mixture of 3.6 g of ethyl 2-chloronicotinate (19.4 mmol), 1.3 g of 4-phenylpyrazole (8.12 mmol), 4.4 g of K2CO3, 40 mg of 18-crown-6 and 30 mg of KI in 30 ml of N,N-dimethylformamide was stirred at 130° C. for 6 hours. For workup, H2O was added and, after extraction with ethyl acetate, the organic phase was washed with H2O and sat. NaCl solution. The crude product obtained after drying and concentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%). In total, 1.9 g of an oil were obtained, which crystallized completely on standing in a refrigerator.

Quelle