4-Benzyloxyphenylacetic acid → 2-Oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate

Participants

Reaction Steps

To a 10° C. stirred solution of 2-(4-(benzyloxy)phenyl)acetic acid (5.0 g, 0.02 mol) in MeOH (50 mL) was added a solution of potassium tert-butoxide (2.43 g, 0.02 mol) in MeOH (50 mL) under an inert atmosphere. The reaction mixture was stirred for 1 h, concentrated in vacuo and the residue was dissolved in DMF (30 mL). Potassium tert-butoxide (3.6 g, 0.03 mmol) was then added followed by 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (10.3 g, 0.05 mol), and the reaction mixture at RT. The reaction mixture was then stirred for an additional 16 h at RT, quenched with water, stirred for an additional 10 min and the precipitated solid was filtered. The crude solid was dissolved in EtOAc (200 mL) and washed with water, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate (3.6 g, 48%) as a solid.

Provenance & Evidence