Ethylene Glycol → 3-[(2-Hydroxyethoxy)methyl]benzonitrile

Participants

Reaction Steps

A solution of ethylene glycol (7.5 g) in DMF (50 ml) under nitrogen at 0° C. was treated portionwise with sodium hydride (1.35 g) and stirred for 0.5 h. 3-Cyanobenzylbromide (4.74 g) was then added and the solution was allowed to warm to room temperature and stirred for 4 h. The solution was then concentrated in vacuo to remove the DMF. The residue was taken up in EtOAc, washed with phosphate buffer (pH=6.5) and water, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography (Biotage, 2×90 g) eluting with 40-60° C. petroleum ether-EtOAc (1:1) to give the title compound (2.62 g). LCMS RT=2.07 min.

Provenance & Evidence