Diethyl Oxalate → Ethyl 4-[2,4-bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]-2,4-dioxobutanoate

Participants

Reaction Steps

To a stirred solution of sodium tert-butoxide (31.5 g, 328 mmol) and diethyl oxalate (60.5 mL, 3 eq.) in THF (250 mL) was slowly added dropwise a solution of 1-[2,4-bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]ethanone (56 g, 149 mmol) in THF (350 mL) at −5° C. After stirring for 1 hour at this temperature, the resulting solution was stirred for further 3 hours at room temperature. The solution was then taken up in 10% citric acid solution (2000 mL) and thoroughly extracted with ethyl acetate. After washing with brine and drying over Na2SO4, the solvent was removed to provide a yellowish residue that was taken up in light petrol ether to remove the excess of diethyl oxalate to afford the quite pure title compound (58 g, 81% yield).

Provenance & Evidence