Reaktion #40831

Reaktionsgleichung

ethyl 5,6-diphenylpyridine-2-carboxylate

Compound 21

ethyl 5,6-diphenylpyridine-2-carboxylate

N,N′-dimethylethylenediamine

trimethylaluminum

→

title compound

1-(5,6-Diphenyl-pyridin-2-yl)-ethanone

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeit was quenched with water
2. 2
   Extraktionthe products were extracted with ethyl acetate
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   EinengenThe filtered solvents were concentrated in vacuo
6. 6
   Sonstigethe residue was purified by silica gel chromatography (15% ethyl acetate in hexane)

Vorschrift

General Procedure O. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 246 mg, 0.81 mmol) in toluene (5 ml) was added N,N′-dimethylethylenediamine (DMEDA, 78.7 mg, 0.89 mmol) and trimethylaluminum (1.2 ml, 2.44 mmol, 2 M in toluene) dropwise under argon at room temperature. After the mixture was refluxed at 112° C. for 2.5 hours, it was quenched with water, and the products were extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over Na2SO4. The filtered solvents were concentrated in vacuo, and the residue was purified by silica gel chromatography (15% ethyl acetate in hexane) to give title compound as a yellow solid.

Quelle