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A Green and Novel Method for the Synthesis of 4,4‐Difluoro‐3‐oxo‐2‐(triphenylphosphoranylidene) δ‐Lactones by Reformatsky Reaction
Author(s) -
Ibrayim Saidalimu,
Fang Xiang,
Zhang Dong,
Liu Lu,
Wu Fanhong
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201180445
Subject(s) - chemistry , reformatsky reaction , tetrahydrofuran , sodium hydroxide , aqueous medium , organic chemistry , aqueous solution , medicinal chemistry , solvent
Abstract In the presence of In/CuCl, ethyl 4‐bromo‐4,4‐difluoro‐3‐oxo‐2‐(triphenylphosphoranylidene)butanoate reacted with various aldehydes in aqueous medium at room temperature to give the α , α ‐difluorinated β ‐hydroxy carbonyl compounds. Furthermore, treating Reformatsky addition compounds with 1 equiv. of sodium hydroxide in the mixture of tetrahydrofuran and water afforded gem ‐di?uoromethylenated 2‐triphenylphosphoranylidene δ ‐lactones in excellent yields.