• 10.1021/jo00430a004
  • The Journal of Organic Chemistry
  • 42 (10)
  • May 2002
  • 1688–1690

Isolation and reactions of .alpha.-lithio N,N-dimethylacetamide

Reproducible Experimental


Summary: The paper discusses the synthesis, reactivity and stability of α-lithio N,N dimethylacetamide.

The paper described carefully the use of various solvents (pentane, THF) and their impact on the formation of the desired product.

It also described the stability of the final compound by quenching the reaction mixture at different conditions of time and temperature.

Finally a table of reactivity of the lithio derivative is presented with various organic halides and carbonyl compounds. Reaction with epoxy is also mentioned.

Reaction of interest:

Our research had an interest in the design and synthesis of chelates for the segregation of actinides and lanthanides in nuclear waste.  We were interested by the formation of α-lithio N,N-dimethylacetamide to allow the formation of mono and bi-functionalized pyridine N-Oxide[1] in order to obtain softer known ligands to favor the desired effect.

The reaction consisted of the deprotonation of N,N-dimethyl acetamide using a strong base (LDA) .

Reproducibility: In our case we chose to reproduce the formation of α-lithio N,N dimethylacetamide using dry THF as solvent. We used it without isolation with our chloroderivative. The procedure reproduced perfectly.

Change and improvement: No changes were required to obtain the desired lithio derivative and the reactivity that occurred was as expected.

[1] J. Heterocyclic Chem., 44, 99 (2007). Synthesis of Propionamide Pyridine and Pyridine N-oxide Ligands: Iris Binyamin, Sylvie Pailloux, Benjamin P. Hay, Brian M. Rapko, Eileen N. Duesler, and Robert T. Paine

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