Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5267098 | Tetrahedron Letters | 2012 | 4 Pages |
Abstract
While optimizing the synthesis of pharmaceutical building block 3 [ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate], we encountered an unusual addition of an aryllithium reagent to the ketone oxygen atom of diethyl ketomalonate. Compound 3 was ultimately prepared on a large scale by a two-step sequence involving (1) annulation of a functionalized Grignard reagent with diethyl ketomalonate and (2) selective mono-reduction of a geminal diester using lithium tri-tert-butoxyaluminum hydride.
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Authors
Benjamin N. Rocke, Edward L. Conn, Shane A. Eisenbeis, Roger B. Ruggeri,