Uncatalyzed reaction of silyl ketene acetals with oxalyl chloride: a straightforward preparation of symmetrical pulvinic acids.

reaction: see text] Several natural pulvinic acids were synthesized. Silyl ketene acetals derived from methyl arylacetates (4 equiv) reacted with oxalyl chloride at -78 degrees C, without the need of adding a catalyst. After treatment of the crude diketones with DBU and acidification with hydrochloric acid, symmetrical pulvinic acids methyl esters were obtained. Saponification of the methyl esters afforded the corresponding pulvinic acids in 60-70% overall yields from oxalyl chloride.

Citation

Benoît Heurtaux, Claude Lion, Thierry Le Gall, Charles Mioskowski. Uncatalyzed reaction of silyl ketene acetals with oxalyl chloride: a straightforward preparation of symmetrical pulvinic acids. The Journal of organic chemistry. 2005 Feb 18;70(4):1474-7

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PMID: 15704989

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