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Emploi du bromure de vinylmagnésium pour la synthèse de molécules marquées au 14 C: Nouvelle méthode de préparation de glycérol 14 C‐1 et d'acide glycérique 14 C‐1
Author(s) -
Pichat L.,
Herbert M.,
Aubert F.
Publication year - 1965
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590010109
Subject(s) - chemistry , medicinal chemistry , saponification , nuclear chemistry , acrylic acid , yield (engineering) , bromine , bromide , organic chemistry , copolymer , materials science , metallurgy , polymer
Acrylic acid 1‐ 14 C is obtained with an 80% yield by carbonation of vinylmagnesium bromide. In desagreement with the literature it has been found that LiAlH 4 reduction of acrylic acid does not give rise to allyl alcohol but mainly to n‐propanol. By successive additions of bromine and diazomethane acrylic acid 1‐ 14 C yields methyl 2‐3 dibromo propionate. Reduction by LiAlH 4 ‐AlCl 3 at −80° C provides 2‐3 dibromo propanol which is converted into 2‐3 diacetoxy‐propanol 1‐ 14 C. Saponification followed by partition chromatopraphy gives glycerol 1‐ 14 C overall yield 35% calculated on Ba 14 CO 3 . Glyceric acid 1‐ 14 C is obtained with an overall yield 43% based on Ba 14 CO 3 from methyl 2‐3 dibromopropionate 1‐ 14 C.