Uses
Ethyl Cyclohexanone-β-carboxylate is an intermediate used to prepare carbazole-carboxamides with selective JAK2 inhibitory activities.
Hazard
Ethyl 3-oxocyclohexane-1-carboxylate is irritating to the eyes and skin, may cause respiratory irritation, and is harmful if swallowed.
Synthesis
To a round bottom flask was added 3-oxo-1-cyclohexanecarboxylic acid (3.85 g, 27.1 mmol), ethanol (7.91 mL), p-toluenesulfonic acid (0.097 g, 0.56 mmol) and toluene (65.9 mL). The mixture was refluxed with a Dean-star trap overnight. The reaction mixture was cooled down and concentrated under reduced pressure to afford 4.61 g (100 %) of the title compound, 3-oxo-cyclohexanecarboxylic acid ethyl ester (Ethyl 3-oxocyclohexane-1-carboxylate), as a yellow oil.
References
[1] Patent: US2011/98299, 2011, A1. Location in patent: Page/Page column 23
[2] Journal of Fluorine Chemistry, 2017, vol. 199, p. 60 - 66
[3] Journal of the Chemical Society, 1909, vol. 95, p. 2016
[4] Patent: WO2014/11902, 2014, A1. Location in patent: Paragraph 00284-00285
[5] Patent: WO2014/194242, 2014, A2. Location in patent: Paragraph 00353; 00356