Hydroxyalkylated Resins

Chemfiles Volume 3 Article 4

Hydroxyalkylated resins are ideal for attaching carboxylic acids. Acylation of (hydroxymethyl)polystyrene provides a benzyl ester linkage cleaved by treatment with HF, trifluoromethanesulfonic acid (TFMSA), or by hydrogenolysis. Transesterification with NaOMe produces methyl esters, alcohols are liberated by reduction employing LiBH4 or diisobutylaluminiumhydride (DIBAH), and aminolysis provides carboxamides. Coupling of carboxylic acids can be performed with standard procedures using symmetrical anhydride/dimethylaminopyridine (DMAP), 2,6-dichlorobenzoyl chloride according to Sieber, active esters/diisopropypethylamine (DIEA), or Mitsunobu coupling reaction.

 

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