Use of solid-supported reagents simplified routine acylation of primary and secondary alcohols because it eliminated traditional purification. Using a parallel synthesizer, eight primary or secondary alcohols reacted with acid chloride in the presence of poly(4-vinylpyridine), which acted as a base and acylation catalyst. Filtration, subsequent addition of amino-functionalized silica gel to remove excess acid chloride and a second filtration affording the corresponding esters in high yield (70-98%), excellent chemical purity (93-99%). Acylation of enantiopure alcohols yielded enantiopure esters. Acylation of two tertiary alcohols gave esters in low yield (27-57%) and variable chemical purity (57-99%).
Bibliographical noteFunding Information:
We thank NSERC (Canada) for financial support and a postgraduate scholarship to K.L.M., Dr. Robert Zamboni (Merck Frosst, Montréal) for the loan of Argonaut Quest 210 parallel synthesizer and Sarah McDermott and Candice Suter for preliminary experiments.