Synthesis 2006(24): 4266-4268  
DOI: 10.1055/s-2006-950307
PSP
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Bestmann-Ohira Reagent

Jörg Pietruszka*, Andreas Witt
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Im Stetternicher Forst Geb. 15.8, 52426 Jülich, Germany
Fax: +49(2461)616196; e-Mail: [email protected];
Further Information

Publication History

Received 19 June 2006
Publication Date:
09 October 2006 (online)

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.

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15

The reagent is meanwhile commercially available from Digital Chemistry DSC (www.digitalchem.com).

17

A 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.