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[ 11 C]Methylenetriphenylphosphorane, a new 11 C‐precursor, used in a one‐pot wittig synthesis of [β‐ 11 C]styrene
Author(s) -
Kihlberg Tor,
Gullberg Per,
Långström Bengt
Publication year - 1990
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.2580281002
Subject(s) - chemistry , styrene , iodide , wittig reaction , epichlorohydrin , methyl iodide , triphenylphosphine , yield (engineering) , benzaldehyde , radiochemistry , nuclear chemistry , one pot synthesis , chemical synthesis , organic chemistry , catalysis , copolymer , biochemistry , polymer , materials science , in vitro , metallurgy
Preparation of [ 11 C]methyltriphenylphosphonium iodide and the in situ generation of [ 11 C]methylenetriphenylphosphorane directly from [ 11 C]methyl iodide, is described. Using this one‐pot preparation, [β‐ 11 C]styrene was synthesized conveniently, fast and with a minimum of manual handling. The synthesis was performed by using [ 11 C]methyl iodide, triphenylphosphine, epichlorohydrin and benzaldehyde in tetrahydrofurane/o‐dibromobenzene, with a synthesis time of 40 min (counted from the end of [ 11 C]methyl iodide transfer), a radiochemical yield of 80–90% of [β‐ 11 C]styrene and a specific radioactivity, of 100MBq/μmol. In a typical experiment starting with 960 MBq 11 C‐methyl iodide, 200 MBq of [β‐ 11 C]styrene was obtained within 42 min.