Cesium Fluoride-Mediated Claisen Rearrangement of Aryl Propargyl Ether. Exclusive Formation of 2-Methylarylfuran and Its Availability as a Masked Salicylaldehyde

Hisashi ISHII; Tsutomu ISHIKAWA; Sunao TAKEDA; Satoshi UEKI; Masahiro SUZUKI

doi:10.1248/cpb.40.1148

Hisashi ISHII, Tsutomu ISHIKAWA, Sunao TAKEDA, Satoshi UEKI, Masahiro SUZUKI

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Keywords: cesium fluoride, Claisen rearrangement, aryl propargyl ether, arylpyran, 2-methylarylfuran, furan ring cleavage, osmium tetroxide oxidation, masked salicylaldehyde

JOURNALS FREE ACCESS

Volume 40 (1992) Issue 5 Pages 1148-1153

DOI https://doi.org/10.1248/cpb.40.1148

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Abstract

Claisen rearrangement of an aryl propargyl ether in the presence of CsF led to exclusive formation of 2-methylarylfuran in excellent yield. The result of a precise examination of the rearrangement is described. Satisfactory transformation of the 2-methylarylfuran to a salicylaldehyde derivative was achieved by stepwise oxidation. This combination of reactions serves as a useful method for regioselective introduction of a C₁ unit at the ortho position of a phenol group.

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