Reaktion #1710156

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

hexane ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder heating
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Waschenwashed with water and brine
4. 4
   Trocknendried over anhydeous sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residues obtained

Vorschrift

Process 1: Under argon atmosphere, a 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 for 23 hours under heating. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydeous sodium sulfate, and concentrated in vacuo. The residues obtained were subjected to silica gel column chromatography (hexane/ethyl acetate=2:1), to obtain methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoate (20.9 g, 51%) as a brown oil.

Quelle