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I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere.

I have been doing the reaction and I can observe conversion of starting material (nitrile compound) by HPLC analysis. However there are multiple peaks observed.

The article I am following reports using NaHCO3:Na2CO3 1:1 buffer for the work up. The reaction mixture was added to the buffer with stirring under 5ºC and precipitation was observed. Been attempting to do that, but no precipitation is observed. Instead it is forming an oil that floats on top. Anyone who has worked on something similar or who can advise?

  • $\begingroup$ Does the procedure you are using describe the preparation of this exact compound? Do you have any evidence of formation of your required product? $\endgroup$
    – Waylander
    Oct 13, 2023 at 12:41
  • $\begingroup$ so far i have no evidence. I can only see conversion of starting material by HPLC. The NMRs i have run so far, only one of it where i could see 3 all the methyls accounted for on the non aromatic side. But the aromatic side order of splitting was not as expected $\endgroup$
    – Bree
    Oct 16, 2023 at 4:41
  • $\begingroup$ Do you have access to LC/MS? $\endgroup$
    – Waylander
    Oct 16, 2023 at 6:33


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