Erythromycin → Erythromycin A enol ether

Participants

Reaction Steps

A solution (710.0 mL) of EMA (erythromycin A; 104.4 g, 16.90 mmol) in glacial acetic acid was stirred at room temperature for 2 hr, and aqueous NaHCO3 solution was slowly added to neutralize the solution. The reaction mixture was extracted with CHCl3, and the organic layer was dried over Na2SO4. The residue was filtrated, and the filtrate was concentrated to give a crude product (99.30 g). The obtained crude product was dissolved in CHCl3 (250 mL), and the solution was recrystallized by adding hexane (50 mL) to give EM201 (74.50 g, 71%) as a white powder.

Provenance & Evidence