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Efficient Synthesis of Methyl 2‐( tert ‐Butyl)acrylate and Analogous Esters
Author(s) -
Xu LongHe,
Kündig Ernst Peter
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770603
Subject(s) - chemistry , methyl acrylate , allylic rearrangement , reagent , acrylate , acetone , lewis acids and bases , medicinal chemistry , organic chemistry , catalysis , polymer , monomer , copolymer
The title products are prepared via an efficient three‐step synthesis which involves hydroalumination of methyl propiolate and Lewis ‐acid‐promoted reaction with acetone in the presence of BF 3 followed by two highly selective S N 2′ reactions. The key step is the reaction of 2‐(chloromethyl)acrylates with R 2 CuLi/ZnCl 2 reagents which takes place with complete allylic rearrangement.