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Silica gel‐assisted reduction of nitrostyrenes to 2‐aryl‐2‐[ 2 H]‐1‐nitroethanes with sodium borodeuteride
Author(s) -
Sinhababu Achintya K.,
Borchardt Ronald T.
Publication year - 1983
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.2580200814
Subject(s) - chemistry , silica gel , aryl , deuterium , sodium , chloroform , medicinal chemistry , organic chemistry , nuclear chemistry , alkyl , physics , quantum mechanics
Abstract Reduction of nitrostyrenes with sodium borodeuteride in the presence of silica gel (70‐270 mesh) in a mixture of chloroform and 2‐propanol gave the corresponding deuterated nitroethanes in near quantitative yields, free of dimeric products with 72‐81% deuterium incorporation. The method was applied to the synthesis of 2‐phenyl‐, 2‐[4‐methoxyphenyl]‐, 2‐[3,4‐dimethoxyphenyl]‐, 2‐[3,4,5‐trimethoxyphenyl]‐, and 2‐[2,4,5‐trimethoxyphenyl]‐2‐[ 2 H]‐l‐nitroethanes.