Reaktion #716222

Reaktionsgleichung

2-[5-(bromomethyl)pyridin-2-yl]benzonitrile

methyl 3-oxoheptanoate

diisopropylethylamine

lithium chloride

→

methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoate

Ausbeute 51.0%

Lösungsmittel

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder heating for 23 hours
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Waschenwashed with water and brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated in vacuo

Vorschrift

Process 1: Under argon atmosphere, tetrahydrofuran (900 mL) solution of 2-[5-(bromomethyl)pyridin-2-yl]benzonitrile (31.9 g, 117 mmol), methyl 3-oxoheptanoate (27.8 g, 176 mmol), diisopropylethylamine (31.0 g, 240 mmol), and lithium chloride (8.2 g, 193 mmol) was refluxed under heating for 23 hours. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residues were subjected to silica gel column chromatography (hexane/ethyl acetate=2:1) to give methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoate (20.9 g, 51%) as brown oil.

Quelle