For the P-31 NMR samples I simply sampled about 10 µL and dissolved in CDCl3. For the TLC, I took 20 µL and extracted with about 50 µL each of 5% aqueous LiCl and ethyl acetate. The percentage of the peak area at 11.2 ppm went down from the first time point to the second. Two new, broad peaks are visible that were not visible before, but they both have very low signal-to-noise. The reaction picked up a brown color with time. I am not sure what any degradation product might be.
I also spiked the first time point for the TsOCH2P(O)(OEt)2 reaction with an internal standard of diethyl phosponomethyltoluenesulfonate, and the peak near 15.2 ppm increased in intensity, confirming its assignment. What is odd about this reaction is that the first and second second time points had similar ratios of peak areas to each other. It is also odd that there was still diethyl phosphonomethyltoluenesulfonate left at time point 2; I set up the reaction to have PhSO2Na in 20% excess. Perhaps there is water present in this salt, or perhaps my technique was not good. I have not yet performed an internal standard experiment with authentic product, but I am fairly confident that the peak near 11.2 is the product, based on similar molecules.