Acetic Acid → methyl N-formyl-alpha-(3-methoxycarbonylcyclobutylidene)glycinate

Participants

Reaction Steps

To a suspension of sodium hydride (0.27 g, 6.63 mmol, 60% oil dispersion) in dry tetrahydrofuran (10 ml), was added dropwise with vigorous stirring a solution of 3-methoxycarbonylcyclobutanone (0.707 g, 5.52 mmol) and methyl isocyanoacetate (0.6 g, 6.07 mmol) in dry tetrahydrofuran (20 ml) over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours, cooled to 0° C. and 10% aqueous acetic acid (20 ml) added dropwise. The organic solvent was removed in vacuo and the resulting solution extracted with dichloromethane (3×20 ml). The combined extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated to give an oil. The crude product was purified by flash chromatography, eluting with ethyl acetate-hexane (1:1, 3:2), to give methyl N-formyl-α-(3-methoxycarbonylcyclobutylidene)glycinate as a colourless oil.

Provenance & Evidence