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[Study on the phosphorylaions reaction between ethyl salicylate and DEPH].

Guang pu xue yu guang pu fen xi = Guang pu (2005-03-12)
Xiao-lan Chen, Xin-cheng Liao, Jian-sha Lu, Lei Guo, Ling-bo Qu, Yu-fe Zhao
ABSTRACT

Atherton-Todd reaction has been extensively applied to the synthesis of phosphates and phosphoroamidates. Under Atherton-Todd reaction conditions, dialkyl phosphites were probably transformed into diakyl phosphorochloridates. We have tried to use Atherton-Todd reaction to synthesize phosphate of salicylic-acid. But when the -COOH of salicylic acid was under unprotected, the yield was quite low. It was found that the -COOH possibly participated in the reaction. The competitive reaction between the -COOH and -OH of salicylic acid probably existed. In order to understand the detail mechanism, ethyl-salicylate was selected to be phosphorylated In the end, ethyl-salicylate successfully phosphorylated by modification of the classical Atherton-Todd procedure through dropping the DEPH and tetrachloromethane into the mixed solution of ethyl-salicylate, triethylamine and dioxane with good yields. The structures were elucidated by NMR and ESI/MS/MS data.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl salicylate, 99%
Sigma-Aldrich
Ethyl salicylate, ≥99%, FCC, FG

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