Regiochemistry of the Reaction of 2-Acylcyclohexanones with Trimethyl Orthoformate: A Convenient One-Pot Method to Obtain 7,7-Dimethoxy Alkanoate Methyl Esters

Marcos A. P. Martins; Giovani P. Bastos; Adilson P. Sinhorin; Alex F. C. Flores; Helio G. Bonacorso; Nilo Zanatta

doi:10.1055/s-1999-2725

Synlett 1999; 1999(6): 789-791
DOI: 10.1055/s-1999-2725

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Regiochemistry of the Reaction of 2-Acylcyclohexanones with Trimethyl Orthoformate: A Convenient One-Pot Method to Obtain 7,7-Dimethoxy Alkanoate Methyl Esters

Marcos A. P. Martins^* , Giovani P. Bastos, Adilson P. Sinhorin, Alex F. C. Flores, Helio G. Bonacorso, Nilo Zanatta

^*Departamento de Química, Universidade Federal de Santa Maria, 97.105-900 Santa Maria, RS, Brazil; Fax +55 55 2 20 80 31; E-mail: mmartins@base.ufsm.br http://www.ufsm.br/nuquimhe

Abstract

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The regiochemistry of the reaction of 2-acylcyclohexanones [containing 2-acyl groups, C(O)R, where R = Me, Et, CH₂Ph, CF₃, Ph and OMe] with trimethyl orthoformate to obtain the corresponding acetal derivative is reported. Compounds with R = alkyl groups showed to be convenient synthons for a one-pot method to obtain 7,7-dimethoxy alkanoate methyl esters under mild conditions. The results of the reaction of 2-acetylcyclopentanone, -heptanone and -octanone with trimethyl orthoformate are also reported.

acetals - β-diketones - 2-acylcycloalkanones - trimethyl orthoformate - reverse Claisen condensation

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