Could someone suggest some suitable protocol for the reaction of NHS ester and alcohol?

Aleksandra Stojanovic @Aleksandra-Stojanovic-4

02 March 2020 1 6K Report

I'm searching for the reaction between an activated NHS ester and cyclic alcohol. The alcohol (cyclic one)should attack the ester carbon, and N-hydroxysuccinimide should be released.

I have tried to make an ester directly from the carboxylic acid and cyclic alcohol, in the reaction with EDC and DMPA in dried THF but unsuccessfully. Also, before that, I've tried to synthesize the same ester in two steps. In the first one, I synthesized an acid chloride which was supposed to react with cyclic alcohol, but the reaction was unsuccessful too.

Michael G. Weller

Often such reactions fail due to traces of water present. Not only the solvent needs to be dry, but all other reagents, too. Air moisture is detrimental, also.

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