[H-].[Na+:2].[C:3]([O:6][CH2:7][CH3:8])(=[O:5])[CH3:4].[CH:9](OCC)=[O:10]>C(OC(C)C)(C)C>[CH2:7]([O:6][C:3]([CH:4]=[CH:9][O-:10])=[O:5])[CH3:8].[Na+:2]To a suspension of sodium hydride (60% dispersion in oil) (269 g, 16.7 mol) in isopropyl ether (12 L) was slowly added ethyl acetate (1280 g, 14.2 mol) at such a rate as to maintain an internal temperature of 45° C. Ethyl formate (2232 g, 30.13 mol) then added dropwise at 42° C. and stirred at ambient temperature for 18 h. The mixture was filtered and washed with ethyl ether (2×300 mL), with hexanes (500 mL) and the solid was dried to give sodium 2-ethoxycarbonyl ethenolate as a white solid (1930 g, 99%); 1H NMR (DMSO-d6, 300 MHz) δ1.03 (t.3H), 3.86 (q, 2H), 4.08(d, 1H), 8.03 (d, 1H).
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