Regioselective synthesis of 4-acetyl- and 5-acetyl-3-methylisoxazole: Their conversion into silyl- and methyl enol ethers

Article abstract of DOI:10.1080/00397919208021114

Acetonitrile oxide reacts regioselectively with 3-buten-2-one and (E)-4-methoxy-3-buten-2-one to give 5-acetyl- 2 and 4-acetyl-3-methylisoxazole 3, respectively. Treatment of ketones 2 and 3 with trimethylsilyl trifluoromethanesulfonate gave the silyl enol ethers 4 and 5, whereas the methyl enol ethers 8 and 9 were obtained via elimination of methanol from the corresponding dimethyl ketals.

Full text of DOI:10.1080/00397919208021114

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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Regioselective Synthesis of
4-Acetyl-and 5-Acetyl-3-
methylisoxazole: Their
Conversion into Silyl-and
Methyl Enol Ethers
Stefano Chimichi a & Barbara Cosimelli a
a Dipartimento di Chimica Organica e Centro CNR
sulla Chimica e la Struttura dei Composti Eterociclici
e loro Applicazioni, Via Gino Capponi 9, 1-50121,
Firenze, Italy
Published online: 23 Sep 2006.
To cite this article: Stefano Chimichi & Barbara Cosimelli (1992) Regioselective
Synthesis of 4-Acetyl-and 5-Acetyl-3-methylisoxazole: Their Conversion into Silyl-
and Methyl Enol Ethers, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 22:20, 2909-2920, DOI:
10.1080/00397919208021114
To link to this article: http://dx.doi.org/10.1080/00397919208021114
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