Sodium Hydroxide → HCID 68501669, compound

Participants

Reaction Steps

A mixture of A1 (1 eq) in AcOH, conc. HCl and H2O (1:2:1, 0.065 M) was heated at reflux overnight, then cooled to RT and diluted with H2O and EtOAc and separated. The aqueous phase was washed with EtOAc and the combined extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The crude was dissolved in AcOH and NaOAc (2 eq) was added. The resulting solution was heated at reflux for 1 hr. The reaction mixture was cooled and the mixture was extracted with EtOAc. The organic phase was washed twice with brine, dried (Na2SO4) and the solvent removed under reduced pressure. The residue was taken up in H2O and to the resulting suspension was added an aqueous solution of 23 M NaOH (8 eq) and heated to 90° C. for 30 min. The reaction solution was cooled then acidified to pH 4 with 2 M HCl. The mixture stirred for 10 min and filtered. The resulting solid was washed sequentially with H2O, hexanes, Et2O, EtOAc and dried under high vacuum to give the title compound as a pale orange powder.

Provenance & Evidence