Synthesis of ω-Hydroxy Carboxylic Acids and α,ω-Dimethyl Ketones Using α,ω-Diols As Alkylating Agents

Autor:	Kensaku Maeda, Yosuke Iuchi, Megumi Hyotanishi, Brittany E. Miller, Yasushi Obora, Yasutaka Ishii
Rok vydání:	2010
Předmět:	Diketone chemistry.chemical_classification chemistry.chemical_compound Ketone chemistry Carboxylic acid Organic Chemistry Diol Alkylation Chemical synthesis Medicinal chemistry Cyclopentadecanolide Muscone
Zdroj:	The Journal of Organic Chemistry. 75:1803-1806
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9027165
Popis:	Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl diketones was successfully achieved by using alpha,omega-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of [IrCl(cod)](2) or [IrCl(coe)(2)](2) gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of [IrCl(cod)](2) and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2033fe3ba165e0eace927515e3e05a1d https://doi.org/10.1021/jo9027165 Zobrazit plný text záznamu