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Please login to access the full content or check if you have access via Method 1: Stepwise Esterification of Phosphoryl Chloride

DOI: 10.1055/sos-SD-042-00920

McKenna, C. E.; Kashemirov, B. A.; Błażewska, K. M.Science of Synthesis, (200942812.

This method is used for the preparation of simple dialkyl phosphates, but can also be applied to the synthesis of more-complex biophosphates, e.g. phosphatidylcholines 92, which are of interest as enzyme inhibitors, cardiac agents, and antifungal, antimicrobial, and antitumor agents. Stepwise diesterification of phosphoryl chloride in the presence of a tertiary amine, first by a long-chain alkoxy alcohol 91 and then by (2-hydroxyethyl)trimethylammonium 4-toluenesulfonate (choline 4-toluenesulfonate) provides a convenient and simple route to these compounds (Scheme 29).[‌88‌,‌89‌] Typically, the first esterification step is complete in 13h, whereas the second step requires 2 days.

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