ChemInform Abstract: 1,4-Addition of an Aryllithium Reagent to Diethyl Ketomalonate. Scalable Synthesis of Ethyl 1-(Hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate

Autor:	Benjamin N. Rocke, Edward L. Conn, Shane A. Eisenbeis, Roger B. Ruggeri
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Annulation Ketone Geminal Hydride chemistry.chemical_element General Medicine Medicinal chemistry chemistry.chemical_compound chemistry Reagent Organic chemistry Lithium Hydroxymethyl Carboxylate
Zdroj:	ChemInform. 44
ISSN:	0931-7597
DOI:	10.1002/chin.201301099
Popis:	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.
Databáze:	OpenAIRE
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