✦ LIBER ✦

Synthesis of cyclopropyl cyanide-2,2-d2

✍ Scribed by William B. Edwardsiii; David F. Glenn

Publisher: John Wiley and Sons
Year: 1976
Tongue: French
Weight: 268 KB
Volume: 12
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580120117

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

A convenient method for the synthesis of cyclopropyl cyanide‐2,2‐d~2~ has been elaborated. Reduction of methyl 3‐cyanopropionate with lithium borodeuteride followed by reaction of the resulting alcohol with triphenylphosphine and carbon tetrachloride gave 4‐chlorobutyronitrile‐4,4‐d~2~. Conversion of the chloride to the iodide with sodium iodide followed by cyclization with sodium hydride afforded cyclopropyl cyanide‐2,2‐d~2~ in 30% overall yield with deuterium incorporation of > 95%.

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