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Synthesis 2016; 48(13): 2050-2056
DOI: 10.1055/s-0035-1561601
DOI: 10.1055/s-0035-1561601
psp
An Expeditious Synthesis of 8-Methoxy-1-tetralone
Weitere Informationen
Publikationsverlauf
Received: 16. Februar 2016
Accepted after revision: 14. März 2016
Publikationsdatum:
20. April 2016 (online)


Abstract
8-Methoxy-1-tetralone was synthesized in a concise and efficient manner involving a sequential palladium-mediated cross-coupling reaction (Heck), catalytic hydrogenation, and intramolecular acylation mediated by Eaton’s reagent or Lewis acids. The pivotal step in the synthesis was the use of a bromine substituent at the benzenoid C4 position of the intermediate methyl 4-arylbutyric ester to ensure cyclization ortho to the methoxy moiety and obviate cyclization at the para position to the thermodynamically preferred 6-methoxy-1-tetralone, the sole product obtained in the absence of this blocking group.
Key words
8-methoxy-1-tetralone - Eaton’s reagent - Heck reaction - intramolecular acylation - Lewis acidsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561601. 1H, 13C and 2D NMR spectra of all compounds described are included.
- Supporting Information