I'm trying to make the tosylate of dimethylaminoethanol, but I am having trouble isolating the product as I find it degrades following work-up. Can anybody suggest any work-up conditions which will avoid degradation? Currently, I'm doing the reaction in THF using triethylamine as base. When the reaction is complete, I add water to dissolve the salt formed and then wash with ethyl acetate. TLC analysis of each organic washing shows that the product is still there, but when I remove the solvent in vacuo I am only left with starting material. Thanks in advance.