Enol ethers and acetals: acylation with dichloroacetyl, acetyl and benzoyl chloride in ionic liquid medium

TETRAHEDRON LETTERS

卷:53

Article

Guarda, Emerson A.²  Marzari, Mara R. B.¹  Frizzo, Clarissa P.¹  Guarda, Patricia M.²  Zanatta, Nilo¹  Bonacorso, Helio G.¹  Martins, Marcos A. P.¹ 

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

[2] Fdn Fed Univ Tocantins, Chem Lab, BR-77001090 Palmas, TO, Brazil

关键词: Enol ethers;    Acylation;    Ionic liquids;    Acetals;   

DOI  :  10.1016/j.tetlet.2011.10.163

来源: Elsevier

【 摘 要 】

Synthesis of 4-alkoxy-1,1-dichloro-3-alken-2-ones [CHCl2C(O)C(R-2=C(R-1)-OR, where R, R-1, R-2 = Et, H, H; Me, Me, H; Et, H, Me; Me, -(CH2)(2)-; Me, -(CH2)(3)-; Et, Et, H; Et, Bu, H; Et, i-Pr, H; Et, i-Bu, H; Me, Ph, H; Me, thien-2-yl, H] from acylation of enol ethers and acetals with dichloroacetyl chloride, in ionic liquid ([BMIM]BF4] or [BMIM][PF6]) is reported. The synthesis of alkenones [R-3-C(O)C(R-2=C(R1)-OR], where R/R-1/R-2/R-3 = Et/H/H/Ph, t-Bu/H/H/Ph, Me/-(CH2)(4)/Ph. Me/-(CH2)(4)/Me] from the reaction of enol ethers with benzoyl chloride or acetyl chloride, in ionic liquid [BMIM][BF4], is also reported. Last products are described for the first time. (C) 2011 Elsevier Ltd. All rights reserved.

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