175352-88-2Relevant academic research and scientific papers
Organophosphorus chemistry. Part 1: The synthesis of alkyl methylphosphonic acids
Timperley, Christopher M.,Bird, Michael,Holden, Ian,Black, Robin M.
, p. 26 - 30 (2001)
Several alkyl hydrogen methylphosphonates of structure RO(HO)P(O)Me were synthesised by a three-stage route [R =i-Pr, n-Bu, i-Bu, s-Bu, pinacolyl Me3C-CH(Me)-, cyclopentyl and cyclohexyl]. Trimethyl phosphite was transesterified with alcohols in the presence of sodium catalyst to give the mixed phosphites (MeO)2POR in 6-64% yield. Treatment of these with methyl iodide gave alkyl methyl methylphosphonates RO(MeO)P(O)Me in 66-95% yield. Selective demethylation of these compounds by bromotrimethylsilane, followed by methanolysis of the phosphorus silyl esters RO(Me3SiO)P(O)Me, gave the hydrogen phosphonates in 60-97% yield.
Phosphitylation via the Mitsunobu reaction
Grice, I. Darren,Harvey, Peta J.,Jenkins, Ian D.,Gallagher, Michael J.,Ranasinghe, Millagahamada G.
, p. 1087 - 1090 (2007/10/03)
Treatment of a dialkyl phosphite with triphenylphosphine and diisopropyl azodicarboxylate in toluene, followed by addition of an alcohol, results in the formation of the corresponding trialkyl phosphite. Similarly, dialkyl phosphonites can be synthesised from monoalkyl phosphites (alkyl phosphinates).
