Uses
ethyl 3-oxocyclopentane-1-carboxylate is an ester derivative and can be used as a pharmaceutical intermediate.
Synthesis
GENERAL METHOD: 3-Oxo-1-cyclopentanecarboxylic acid (63.0 g, 0.443 mol) was dissolved in ethanol (950 mL) at 15 °C and thionyl chloride (SOCl2, 38.8 mL, 0.532 mol) was slowly added. The reaction mixture was stirred at room temperature overnight, followed by concentration under reduced pressure. The residue was dissolved in chloroform (CHCl3, 500 mL) and stirred with saturated aqueous sodium bicarbonate (NaHCO3) solution (200 mL) for 30 minutes. The organic and aqueous layers were separated and the aqueous layer was further extracted with chloroform (2 x 50 mL). All organic phases were combined and dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum. Finally, the residue was purified by distillation under reduced pressure to afford the target product ethyl 3-oxocyclopentanecarboxylate.
References
[1] Journal of Fluorine Chemistry, 2017, vol. 199, p. 60 - 66
[2] Journal of the Chemical Society, 1908, vol. 93, p. 575
