Reaktion #1446544

Reaktionsgleichung

2-bromo-6-(3-pyrroline-1-yl)pyridine

2-bromo-6-(pyrrolidine-1-yl)pyridine

ammonium chloride

benzylmagnesium chloride

→

title compound

2-Benzyl-6-(3-pyrroline-1-yl)pyridine

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic phase was washed with aqueous saturated sodium chloride
3. 3
   Sonstigethe solvent was removed
4. 4
   Wascheneluted with hexane

Vorschrift

72.3 ml of a tetrahydrofuran solution containing 1.07 mol of benzylmagnesium chloride was added dropwise into a mixture of 11.6 g of a mixture of 2-bromo-6-(3-pyrroline-1-yl)pyridine and 2-bromo-6-(pyrrolidine-1-yl)pyridine and 20 ml of tetrahydrofuran containing 1.4 g of 1,3-bis(diphenylphosphino)propanenickel(II) chloride over 10 minutes in an ice bath. After cooling at room temperature overnight, the reaction solution was poured into aqueous saturated ammonium chloride and extracted with ethyl acetate. The organic phase was washed with aqueous saturated sodium chloride and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane and then with hexane/ethyl acetate (20:1), to give 11.8 g of the title compound as a mixture with 2-benzyl-6-(pyrrolidine-1-yl)pyridine.

Quelle