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Synthesis of 14 C labelled acrylic derivatives: Diethyl [3‐ 14 C] methylidenemalonate and isobutyl [3‐ 14 C] cyanoacrylate
Author(s) -
De Keyser JeanLuc,
De Cock Christian J. C.,
Poupaert Jacques H.,
Dumont Pierre
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270807
Subject(s) - chemistry , adduct , maleic anhydride , diethyl malonate , knoevenagel condensation , paraformaldehyde , diethyl ether , organic chemistry , anthracene , cyanoacrylate , polymer chemistry , medicinal chemistry , catalysis , copolymer , polymer , adhesive , layer (electronics)
Isobutyl [3‐ 14 C] cyanoacrylate and diethyl [3‐ 14 C] methylidenemalonate were synthesized by the intermediate of their protective Diels‐Alder adduct with anthracene. These adducts ( 2a‐b ) were obtained in a one‐pot procedure by Knoevenagel condensation of [ 14 C] paraformaldehyde with isobutyl cyanoacetate and diethyl malonate respectively in the presence of a basic catalyst and anthracene. The adducts are stable crystalline compounds easily purified by recrystallization. The olefinic target coumpounds ( 1a‐b ) were obtained in high chemical and radiochemical purity (>99%) by thermolysis at 220 °C in mineral oil in the presence of maleic anhydride.