Sodium Hydroxide → HCID 15462808, compound

Participants

Reaction Steps

To a solution of ethyl 2-(4-methoxybenzyl)-3-oxobutyrate in EtOAc stirred at ice bath temperature under an argon atmosphere is added an aquious solution of NaOH. This is immediately followed by the addition of an aqueous solution of pyrid-2-yldiazonium chloride [prepared from 2-aminopyridine in 6 N HCl and NaNO2 ]. The mixture is partitioned between EtOAc and H2O. The aqueous layer is washed with EtOAc. The combined organic extracts are washed with saturated aqueous NaCl solution, dried (Na2SO4) and the solvent is removed in vacuo. The residue is dissolved in EtOH and the solution is saturated with HCl gas. This is refluxed then cooled to room temperature and partitioned EtOAc and saturated aqueous NaHCO3 solution. The aqueous layer is washed with EtOAc. The combined organic extract is washed with H2O then saturated aqueous NaCl solution, dried (Na2SO4) and the solvent is removed in vacuo. The residue is purified by chromatography to afford the title compound.

Provenance & Evidence