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Synlett 2000; 2000(9): 1339-1341
DOI: 10.1055/s-2000-7154
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Synthesis and Reactivity of a Solid-Supported Dialkoxybenzaldehyde with an Extended Spacer

Lalgudi S. Harikrishnan* , H. D. Hollis Showalter
  • *Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Company, 2800 Plymouth Road, Ann Arbor, Michigan 48105 USA; Fax (5 18)-2 57-20 19; E-mail: LalH@albmolecular.com
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Publication Date:
31 December 2000 (online)

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Starting from Merrifield resin, a high-yielding, four-step synthesis of 4-(4-formyl-3-methoxyphenoxy)butyl polystyrene (2) is reported. All intermediates were converted to simple derivatives so that approximate loadings could be determined by elemental analysis. The reactivity of the aldehyde resin 2 so formed was evaluated by carrying out sequential reductive amination and amidation reactions, followed by resin cleavage, to obtain product 7 in good yield and purity.

solid-phase synthesis - combinatorial chemistry - aldehyde resin - hydroboration - reductive amination