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Silica gel-assisted reduction of nitrostyrenes to 2-aryl-2-[2H]-1-nitroethanes with sodium borodeuteride

✍ Scribed by Achintya K. Sinhababu; Ronald T. Borchardt

Publisher: John Wiley and Sons
Year: 1983
Tongue: French
Weight: 263 KB
Volume: 20
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580200814

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✦ Synopsis

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.

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