Efficient Synthesis of Methyl 2-(tert-Butyl)acrylate and Analogous Esters

Efficient Synthesis of Methyl 2-(tert-Butyl)acrylate and Analogous Esters

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 BF3 followed by two highly selective SN2′ reactions. The key step is the reaction of 2‐(chloromethyl)acrylates w...

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Veröffentlicht in:Helvetica chimica acta 1994-09, Vol.77 (6), p.1480-1484
Hauptverfasser: Xu, Long-He, Kündig, Ernst Peter
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung: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 BF3 followed by two highly selective SN2′ reactions. The key step is the reaction of 2‐(chloromethyl)acrylates with R2CuLi/ZnCl2 reagents which takes place with complete allylic rearrangement.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19940770603