The influence of the base. In solution, the standard procedure for the Knoevenagel condensation involves the use of an organic base (e.g. piperidine). However, in some cases, the reaction occurs without a base. In our study, we observed that the reaction between 1 and 4a did not take place in the absence of a base (entry 2). Inorganic bases offer advantages such as improved safety, lower cost, and easier removal. We tested LiOH, NaOH, and Cs2CO3, all of which facilitated product formation, with LiOH providing the highest yield of Z-5a (73 %). Triethylamine, known to assist Knoevenagel condensations by acting as both a catalyst and solvent, was also tested, but in this case, no conversion was detected (entry 6). Piperidine, being a liquid base, can also help in the synthes is by acting as a solvent, providing liquid-assisted grinding conditions (LAG, η < 1), following the same concept as trimethylamine. The use of piperidine under mechanochemical conditions (η = 0.6 -0.9) proved highly efficient, yielding Z-5a in 77% yield (entry 7), and the product was obtained as the Z-isomer with high stereoselectivity. The influence of milling auxiliary. It has been demonstrated that the use of a milling auxiliary can help to increase the efficiency of synthesis under mechanochemical conditions, improving yields and facilitating the recovery and isolation of products. In this study, we tested Al₂O₃ (both basic and neutral forms, typically used as an alternative to silica in organic synthesis for chromatography, but also useful as an abrasive in mechanochemistry due to its hardness), silica (SiO₂, acidic and used for chromatography), TiO₂ (neutral and surface-active), and NaCl (neutral and surface-inactive). We found that the intrinsic basicity of basic alumina was enough to carry the Knoevenagel condensation though with low yield (entry 9). Combining basic alumina with LiOH significantly improved conversion and yield to levels similar to those without a milling auxiliary, while greatly simplifying product recovery, but adding the necessity of employing organic solvents such as methanol to extract the final product. Changing to piperidine combined with basic alumina the reaction proceeded in lower yields. Notably, only basic alumina was effective, while neutral alumina produced negligible amounts of product, even in the presence of LiOH (likely functioning as a diluting agent). Acidic SiO₂ yielded little to no product, even with LiOH.