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Synthesis of carbon-13 labeled 5-(diethylphosphono)-2-pentanone ethylene ketal, a reagent for synthesis of multi C-13 labeled steroids

✍ Scribed by Joseph I. Degraw; Pamela H. Christie; Thomas Cairns

Publisher: John Wiley and Sons
Year: 1982
Tongue: French
Weight: 308 KB
Volume: 19
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580190807

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✦ Synopsis

Alkylation o f ethyl acetoacetate-13Cq with eth lene oxide and ethylene oxide-13C2 af Eorded 2-a~etylbutyrolactone-'~C~, (5) and the hexalabeled form (c), respectively. Treatment o f the lactone with an excess of 48% hydrobromic acid effected decarboxylation with bromide displacement t o yield 5-bromo-2-pentanone labeled with 3 or 5 carbon-13 atoms (5).

The bromo ketone was converted to the ethylene ketal with ethylene glycol and p-toluenesulfonic acid catalysis. Displacement of the bromide by sodio diethyl phosphite gave the required ethylene ketals of 5-(diethylphosphono 2-pentanone (I). A convenient process for preparation oE ethylene-l'C2 oxide from a c e t i ~-~~C * acid is also described.

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