Synthesis of 3-Alkylidene(arylidene)isobenfuran-1(3H)-one and Their Derivatives

doi:10.6023/cjoc201312011

Abstract

This paper reports a novel and highly efficient synthesis of 3-alkylidene(arylidene)isobenzofuran-1(3H)-one and the corresponding derivatives. The new method is characterized with raw material easy to get, low manufacturing cost, mild reaction conditions and high yields. Isobenzofuran-1(3H)-one (phthalide) and their derivatives were used as starting material. After reacted through free-radical bromination with N-bromobutanimide (NBS), the starting materials were converted to the corresponding 3-bromoisobenzofuran-1(3H)-one and their derivatives, followed by nucleophilic substitution with triphenylphosphine. Then the corresponding Wittig reagents were obtained through elimination reaction by triethylamine, which further react with fatty aldehydes or aromatic aldehydes to afford the target compounds. Thirteen target products and intermediates are new compounds.

Key words: 3-alkylidene(arylidene)isobenzofuran-1(3H)-one, derivatives, quaternary alkylphosphonium salt, Wittig reaction, synthesis

Cite this article

Zheng Chunzhi, Zhu Xingxing, Zhao Dejian, Jia Hongbin, Zhang Jizhen. Synthesis of 3-Alkylidene(arylidene)isobenfuran-1(3H)-one and Their Derivatives[J]. Chin. J. Org. Chem., 2014, 34(9): 1881-1888.

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