Journal
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Volume -, Issue 1, Pages 26-30Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b007077g
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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)-,dagger cyclopentyl and cyclohexyl]. Trimethyl phosphite was transesterified with alcohols in the presence of sodium catalyst to give the mixed phosphites (MeO)(2)POR 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.
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