Ethyl bromoacetate → 5-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridinone

Participants

Reaction Steps

To a suspension of LiH (45.6 mg) in DMF (6.0 mL) was added portionwise 5-(diphenylmethyl)-2(1H)-pyridinone (500 mg) at ambient temperature and the mixture was stirred at the same temperature for 15 minutes. Ethyl bromoacetate (255 μL) was added dropwise to the mixture. The mixture was stirred at ambient temperature for 14 hours. The reaction was quenched with 1M HCl aqueous solution (10.0 mL) and the mixture was extracted with EtOAc (30 mL). The organic layer was washed successively with saturated NaHCO3 aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=3:2) to afford 5-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridinone (574 mg) as a colorless amorphous.

Provenance & Evidence