Ethyl propiolate → HCID 66759331, compound

Participants

Reaction Steps

To a stirred solution of 1-[2,4-dimethoxy-6-(4-nitrophenoxy)phenyl]-N-hydroxymethanimine (2.06 g, 6.7 mmol) and ethyl propiolate (3.28 mL, 32.4 mmol, 5 eq.) in DCM was slowly added drop wise 15% NaOCl solution (65 mL) at 0° C. After stirring overnight, the organic phase was separated and the aqueous was extracted twice with DCM. The organic phases were pooled and washed with 1 M Na2SO3 solution, then with brine and dried over Na2SO4. The solvent was removed and the residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 8/2 to provide the title compound (1.6 g, 57% yield)

Provenance & Evidence