Abstract
The reaction of methyl 4-hydroxy-trans-2-hexadecenoate [1b] with diiodomethane in the presence of zinc-copper couple yielded methyl 4-methoxy-trans-2,3-methylenehexadecanoate [2] in a 70% yield, together with methyl 4-hydroxy-trans-2,3-methylenehexadecanoate [3] (∼20%). The presence of an allylic hydroxyl group in the α,β-unsaturated ester increases the yield of the cyclopropanation product. The formation ofo-methyl ether reveals the dual role of cyclopropanation and etherification by S.S. reagent of a hydroxylated olefinic compound.
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Ahmad, M.S., Osman, S.M. Simmons-Smith reaction of allylic hydroxylated long chain α, β-unsaturated esters. J Am Oil Chem Soc 57, 363–364 (1980). https://doi.org/10.1007/BF02662060
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DOI: https://doi.org/10.1007/BF02662060