Benzyl Bromide → Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate

Participants

Reaction Steps

A solution of methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate (1.1 g, 4.3 mmol) in DMF (30 ml) was treated with benzyl bromide (0.89 g, 5.2 mmol) and potassium carbonate (0.72 g, 5.2 mmol). The reaction was stirred at ambient temperature overnight and then, partitioned between EtOAc/water. The organic phase was washed well with water, dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2) eluting with CH2Cl2 /EtOAc to give methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.94 g, 53%) as a low melting yellow solid.

Provenance & Evidence