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The synthesis of 14 C ‐3‐ chloro ‐, 3 ‐ bromo ‐ and 3 ‐ iodo ‐propan ‐ 1, 2 ‐ diol and 2, 3 ‐ epoxypropan ‐ 1 ‐01
Author(s) -
Jones A. R.
Publication year - 1973
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.2590090411
Subject(s) - glycidol , diol , chemistry , sodium iodide , labelling , glycerol , iodide , organic chemistry , medicinal chemistry , radiochemistry , catalysis , biochemistry
A convenient procedure has been developed for the synthesis of 14 C‐3‐chloropropan‐1, 2‐diol (α‐chlorohydrin, I ) from 14 C‐glycerol which can also be applied to the preparation of 14 C‐3‐bromopropan‐1, 2‐diol (α‐bromohydrin, III ). These two compounds can be converted, respectively, by nucleophylic displacement with sodium iodide 14 C‐3‐iodopropan‐1, 2‐diol (α‐iodohydrin, II ) and by alkaline epoxidation to 14 C‐2, 3‐epoxypropan‐1‐01 (glycidol, IV ). The use of readily available u, 1, 3‐ or 2‐ 14 C‐glycerol thus enables the title compounds to be synthesised readily and any desired labelling pattern as useful 3‐carbon intermediates for further radioactive syntheses.