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Biotage® PS-TBD Resin Simplifies Williamson Ether Synthesis

11 February 2016

Biotage® PS-TBD is a versatile polymer-supported base, which can facilitate Williamson ether synthesis and may also be used for the N-alkylation of aryl halides, esterification of carboxylic acids, and alkylation of acidic methylenes.

 

PS-TBD resin consists of a bicyclic guanidine moiety (1,5,7-triazabicyclo[4.4.0]dec-5-ene) anchored on polystyrene.In alkylation reactions, the resin may be used in a “catch and release” protocol, whereby an acidic species is caught on the PS-TBD resin as a solid-supported nucleophile.

On reaction with an electrophile, the product is released into solution. By using the electrophile as the limiting reagent, full conversion to product can be achieved, while the excess nucleophile remains bound to the resin. Filtration and solvent evaporation affords the desired product in high purity.

Mode of action of PS-TBD resin forming a bound phenolate.

PS-TBD resin can also facilitate Williamson ether synthesis at room temperature using very mild conditions, as it is effective at deprotonating moderately acidic hydrogen (up to pKa ca 13). Read more about it in the product note below.

The use of PS-TBD resin in the Williamson ether synthesis

Related Documents

Biotage® PS-TBD Polymer Supported Base

Part No: PPS382.V.1 Published: 2016 1.63 MB Format: pdf