I was running an alkylation of malonic ester using NaH in DMF and bromoethane but the reaction failed an I got back my starting material. I started by adding the NaH dropwise to the malonic ester in dry DMF and after 20min I added the bromoethane, warmed to R.T and ran for 12 hours. Any suggestions as to what I can do differently?
Kindly check https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3286627/
Dear Jason Hibbard thanks for the interesting question. First of all it would be interesting to know if you followed a literature procedure. Did you? Then there is one point in your question that puzzles me: How could you possible add the NaH "dropwise"? Sodium hydride is insoluble in organic solvents such as DME. Did you add it as a suspension? My suggestion would be to add the NaH to your malonic ester in DME and wait until the hydride has completely dissolved (perhaps longer than 20 minutes). According to the attached reference the synthesis can also be carried out using sodium ethoxide (freshly prepared by dissolving metallic sodium in ethanol).
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