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Synthesis of deuterium labelled acids
Author(s) -
Kadam A. J.,
Desai U. V.,
Mane R. B.
Publication year - 1999
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/(sici)1099-1344(199909)42:9<835::aid-jlcr244>3.0.co;2-r
Subject(s) - chemistry , decarboxylation , sodium borohydride , furfural , hydrolysis , alkyl , knoevenagel condensation , organic chemistry , benzaldehyde , pyridine , yield (engineering) , sodium ethoxide , acetone , catalysis , materials science , ethanol , metallurgy
Knoevenagel condensation of Meldrum's acid ( 1 ) with benzaldehyde, anisaldehyde, furfural, cinnamaldehyde and acetone gave the corresponding alkylidene derivatives ( 3 ) which were reduced with sodium borohydride to yield alkyl Meldrum's acids ( 4 ). Reaction of ( 4 ) with pyridine‐D 2 O at high temperature furnished α‐dideuterated acids ( 6 ). The reduction of alkylidene derivatives ( 3 ) with sodium borodeuteride yielded β‐deuterated alkyl Meldrum's acids ( 7 ) which on hydrolysis and decarboxylation yielded β‐deuterated acids ( 9 ). α,α,β‐Trideuterated acids ( 11 ) were prepared by hydrolysis and decarboxylation of ( 7 ) with pyridine‐D 2 O. Copyright © 1999 John Wiley & Sons, Ltd.