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Synthesis 2006(24): 4266-4268
DOI: 10.1055/s-2006-950307
DOI: 10.1055/s-2006-950307
PSP
© Georg Thieme Verlag Stuttgart · New York
Synthesis of the Bestmann-Ohira Reagent
Further Information
Received
19 June 2006
Publication Date:
09 October 2006 (online)
Publication History
Publication Date:
09 October 2006 (online)
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Abstract
The conversion of an aldehyde to a terminal alkyne by means of a one-carbon chain extension is a key reaction in organic synthesis. By using dimethyl 1-diazo-2-oxopropylphosphonate, the Bestmann-Ohira reagent, the transformation can be achieved in one pot. A reliable, convenient sequence for the preparation of the Bestmann-Ohira reagent is described.
Key words
alkynes - diazo compounds - carbenoids - phosphorus
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References
The reagent is meanwhile commercially available from Digital Chemistry DSC (www.digitalchem.com).
17A discussion has taken place on whether the use of NaN3 in CH2Cl2 causes explosions during workup (see sodium azide under http://pubs.acs.org./cen/safety). However, changing the solvent (e.g. to THF) should not lead to a false sense of safety.