Recently, i am running one reaction for TMS-ethers,To a solution of the iodolphenol and triethylamine (2 eq) stirring in CH2Cl2(DCM)at 0° under an inert atmosphere, is added drop wise TMS-Cl (10 eq). The result was allowed to warm to room temperature and stirred overnight.After microwork up,I detected it by TLC, and there is no reaction happened because of the same moving pot in TLC as start material.What should i do? may somebody give me some advice?Thanks

It could be that your TMS ether is unstable on silica gel and, therefore, decomposes when you are TLC-ing your reaction mixture. TMS ethers are fairly easily hydrolyzed and phenolic ethers even more so. I suggest taking an NMR of a reaction aliquot...

you can also try running your tlc's on alumina instead of silica... tends to be less damaging to products