Abstract
Abstract The phosphorylation of alcohols by means of N-[2-(dihydrogen phosphoroxy)-5-nitrobenzyl]pyridinium hydroxide (3), which was prepared from 2-(chloromethyl)-4-nitrophenyl phosphorodichloridate (1) through two steps, was demonstrated. Alcohol with a tertiary amino group in its alkyl moiety was readily phosphorylated with 3 to afford the aminoalkyl dihydrogen phosphate in good yield. On the other hand, the phosphorylation of the usual neutral alcohol proceeded only in the presence of a strong base such as triethylamine to give the corresponding alkyl dihydrogen phosphate (9). Thus, several alkyl dihydrogen phosphates 9 were prepared. In this phosphorylation, the formation of alkyl 2-hydroxy-5-nitrobenzyl ether (10) was also observed.
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