Our starting material is a formylpyridine with a hydroxyl group at the 5-position* (edit: the aldehyde is at the two position*), and we wished to protect the oxygen with TBDMS. We found an identical reaction in the literature that used TBDMSCl and triethylamine. We have not yet fully characterized the product, but it was less soluble in CDCl3 than expected. There was what appeared to be a tertiary-butyl group by H-1 NMR, but nothing that looked like CH3Si. Our options are to set the reaction up again, to try a new base (probably imidazole, which is often used), or to try entirely different conditions, such as TMSOTf and lutidine (we have used this combination previously against aliphatic alcohol groups). Does anyone have any thoughts?
*my original post was in error, and I am sorry about any confusion that this created.