Development of 3-methoxy-4-benzyloxybenzyl alcohol (MBBA) resin as polymer-supported synthesis support: Preparation and benzyl ether cleavage by DDQ oxidation

摘要

3-Methoxy-4-benzyloxybenzyl alcohol (MBBA) resin was synthesized by a two-step sequence under microwave irradiation involving the reaction of commercially available Merrifield resin with vanillin, followed by reduction with sodium borohydride. MBBA resin was treated with bromides in the presence of sodium hydride to afford the corresponding resin-bound benzyl ethers. Cleavage of the resin-bound benzyl ethers from the MBBA resin was carried out using 2,3-dichloro-5,6-dicyanobenzoqunone (DDQ) to give the corresponding alcohols in good yields. Moreover, the recovery, regeneration, and reuse of this polymer support could be achieved easily. MBBA resin can be developed as a kind of solid-phase synthesis bead of alcohols.