An optimized and scalable synthesis of propylphosphonic anhydride for general use
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Representative procedures are described
Diethyl propylphosphonate (6).22 To a mixture of 17.4 g (0.73 mol) of NaH (free of mineral oil) in 100 ml of anhydrous THF was added a solution of 50.0 g (0.36 mol) of dry diethyl phosphonate (10) in 50 ml of anhydrous THF at 30–40 °C, and the mixture was stirred overnight. Next, a solution of 49.0 g (0.4 mol) of 1-bromopropane in 50 ml of anhydrous THF was added dropwise and the mixture was heated under reflux for 4 d under an argon atmosphere. To the mixture was slowly added 130 ml of H2O followed by
Acknowledgements
Support for this work was provided by the project IGA VFU Brno 108/2013/FaF.
References and notes (31)
- et al.
Tetrahedron Lett.
(2013) - et al.
Tetrahedron Lett.
(2005) - et al.
Tetrahedron Lett.
(2010) - et al.
Tetrahedron Lett.
(2011) Tetrahedron
(1981)- et al.
Angew. Chem., Int. Ed. Engl.
(1980) Phosphorus Sulfur
(1987)- et al.
Angew. Chem., Int. Ed. Engl.
(1986) - et al.
J. Org. Chem.
(2004) - et al.
Angew. Chem., Int. Ed. Engl.
(1997)
Eur. J. Org. Chem.
(2001)
Synth. Commun.
(2000)
Synlett
(2009)
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