NaOMe, NaOEt, and related bases are widely used in organic synthesis and are readily available in solid form as free-flowing white (or off-white) solids. During research into cross-coupling reactions, our lab in collaboration with Bristol Myers Squibb discovered that these bases undergo rapid decomposition under air through a complex sequence of events. Today we disclose a pre-print in ChemRxiv describing our efforts to understand this phenomenon. It turns out that this process is so pervasive that even “new” commercial lots of these bases can contain almost none of the desired material. This was a long and circuitous detective story that challenged us to use every analytical trick in the book, from Karl Fischer titration to solid state ²³Na NMR.

Read the full story here: https://chemrxiv.org/articles/preprint/An_Under-Appreciated_Source_of_Reproducibility_Issues_in_Cross-Coupling_Solid-State_Decomposition_of_Primary_Sodium_Alkoxides_in_Air/12818234