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Synthesis of deuterated C‐6 and C‐9 flavour volatiles
Author(s) -
Felder Simon,
Rowan Daryl D.
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(199901)42:1<83::aid-jlcr169>3.0.co;2-f
Subject(s) - chemistry , reagent , alkylation , grignard reaction , bromide , catalysis , deuterium , alkyl , medicinal chemistry , alcohol , organic chemistry , iodide , ether , methyl iodide , physics , quantum mechanics
Regiospecific deuterogenation of alkynols and chain extension of deuterated C‐6 alkyl halides by alkylation with malondialdehyde derivatives was used to synthesise a series of deuterated C‐6 and C‐9 flavour volatiles. Reduction of 3‐hexyn‐1‐ol with deuterium gas using Wilkinson's catalyst required protection of the alcohol as the tert ‐butyldimethylsilyl ether to speed reaction and minimise scrambling of deuterium. Deuterogenation of 5‐hexyn‐1‐ol proceeded cleanly without protection to give 5,5,6,6‐ 2 H 4 ‐hexanol which was converted to 5,5,6,6‐ 2 H 4 ‐hexyl bromide and the corresponding Grignard reagent. Reaction of this Grignard reagent with 3‐trimethylsiloxy‐2‐propenal gave 8,8,9,9‐ 2 H 4 ‐2 E ‐nonenal. Deuterogenation of 3‐hexyn‐1‐ol with Lindlar catalyst gave 3,4‐ 2 H 2 ‐3 Z ‐hexenol which was converted to the corresponding iodide and used to synthesise 6,7‐ 2 H 2 ‐2 E ,6 Z ]‐nonadienal and 6,7‐ 2 H 2 ‐2 E ,6 Z ]‐nonadienol. Wilkinson reduction of the tert ‐butyldimethysilyl derivative of 3‐nonyn‐1‐ol was used to synthesize 3,3,4,4‐ 2 H 4 ‐nonanol and 3,3,4,4‐ 2 H 4 ‐nonanal. Copyright © 1999 John Wiley & Sons, Ltd.