Regioselective Synthesis of 4-Acetyl-and 5-Acetyl-3-methylisoxazole: Their Conversion into Silyl-and Methyl Enol Ethers |
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| Authors: | Stefano Chimichi Barbara Cosimelli |
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| Institution: | 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 |
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| Abstract: | 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. |
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