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I want to synthesize an pivaloyloxymethyl ester from a fluorophosphonic acid. The idea is, to make a compound cell permeable that than be cleaved in the cell by enzymes. Apparently, the acid is a very bad nucleophile, so therefore the reaction with chloromethyl pivalate does not seem to work. I have the reaction running know for more than 26 h with 3 eq. of the chloride, but according to LCMS no product is being formed.

reaction scheme

To deal with this problem, my idea was to hydrolyse the chloromethyl pivalate with pure water and let the resulting hydroxymethyl 2,2-dimethylpropanoate react with acid chloride of my starting material. Do you think this is a valid approach? Unintuitively I did not find any similar reactions like this in the literature. What are your thoughts on this?

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  • $\begingroup$ My thoughts on this so far: I attempted the hydrolysis with water and added ACN for better solubility. However, the product is either volatile or the reaction was not yet complete. TLC was not showing strong coloring with CAM/KMnO4. $\endgroup$
    – raptorlane
    Mar 30 at 16:18

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