Studies on Organic Fluorine Compounds. XLV. Synthesis and Regioselective Substitution Reaction of 3-Trifluoromethylfuran

KOSUKE KAWADA, Osamu Kitagawa, YOSHIRO KOBAYASHI

Research output: Contribution to journalArticle

Abstract

3-Trifluoromethylfuran (1) was efficiently synthesized by the reaction of 4-methyloxazole with 3, 3, 3-trifluoropropyne. Lithiation of 1 with n-butyllithium followed by reaction with an electrophile gave the corresponding 2-substituted 3-trifluoromethylfuran (4). Starting from 2-triethylsilyl-3-trifluoromethylfuran (4a), 2-substituted 4-trifluoromethylfurans (6) were synthesized.
Original languageEnglish
Pages (from-to)3670-3674
JournalChemical and Pharmaceutical Bulletin
Volume33
Issue number9
Publication statusPublished - 1985

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Fluorine Compounds
Substitution reactions
n-butyllithium

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Studies on Organic Fluorine Compounds. XLV. Synthesis and Regioselective Substitution Reaction of 3-Trifluoromethylfuran. / KAWADA, KOSUKE; Kitagawa, Osamu; KOBAYASHI, YOSHIRO.

In: Chemical and Pharmaceutical Bulletin, Vol. 33, No. 9, 1985, p. 3670-3674.

Research output: Contribution to journalArticle

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abstract = "3-Trifluoromethylfuran (1) was efficiently synthesized by the reaction of 4-methyloxazole with 3, 3, 3-trifluoropropyne. Lithiation of 1 with n-butyllithium followed by reaction with an electrophile gave the corresponding 2-substituted 3-trifluoromethylfuran (4). Starting from 2-triethylsilyl-3-trifluoromethylfuran (4a), 2-substituted 4-trifluoromethylfurans (6) were synthesized.",
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AU - KOBAYASHI, YOSHIRO

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N2 - 3-Trifluoromethylfuran (1) was efficiently synthesized by the reaction of 4-methyloxazole with 3, 3, 3-trifluoropropyne. Lithiation of 1 with n-butyllithium followed by reaction with an electrophile gave the corresponding 2-substituted 3-trifluoromethylfuran (4). Starting from 2-triethylsilyl-3-trifluoromethylfuran (4a), 2-substituted 4-trifluoromethylfurans (6) were synthesized.

AB - 3-Trifluoromethylfuran (1) was efficiently synthesized by the reaction of 4-methyloxazole with 3, 3, 3-trifluoropropyne. Lithiation of 1 with n-butyllithium followed by reaction with an electrophile gave the corresponding 2-substituted 3-trifluoromethylfuran (4). Starting from 2-triethylsilyl-3-trifluoromethylfuran (4a), 2-substituted 4-trifluoromethylfurans (6) were synthesized.

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JF - Chemical and Pharmaceutical Bulletin

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