Iodine → Ethyl 5-(hydroxy(pyridin-2-yl)methyl)-4'-methylbiphenyl-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

The Grignard reagent was generated by treatment of magnesium (100 mg, 4.3 mmol) with a solution of 2-bromopyridine (600 mg, 3.8 mmol) and iodine (30 mg) in tetrahydrofuran (5 mL) under nitrogen at 60° C. for 1 hour. The mixture was cooled at 0° C. and ethyl 5-formyl-4′-methylbiphenyl-3-carboxylate (332 mg, 1.24 mmol) was added. The reaction mixture was stirred at 0° C. for 2 h and then quenched by addition of 3 mL of 2 N aq. H2SO4. The mixture was extracted with EtOAc (20 mL×2). The combined organic layers were washed with 1 N aq. NaOH, brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was chromatographed to yield a yellow oil.

Provenance & Evidence