1-Diethoxyphosphorylpropan-2-one → Phosphonic acid, (1-acetyl-8-(2-chloro-4-methoxyphenoxy)octyl)-, diethyl ester

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Reaction Steps

[II; Ar is 2-Cl-4CH3OC6H3, Y is O(CH2)7, R is C2H5, R' is CH3CO] was prepared from 0.57 g of lithium hydride, 13.9 g of diethyl acetonylphosphonate and 27.8 g of 7-(2-chloro-4-methoxyphenoxy)heptyl iodide according to the procedure of Example 12(b). The product was chromatographed on Florisil and further purified by preparative thin layer chromatography (TLC) on silica gel to give 5.9 g of diethyl [1-acetyl-8-(2-chloro-4-methoxyphenoxy)octyl]phosphonate as a yellow oil; MIC vs. herpes simplex type 2=6 mcg/ml. The NMR spectrum was consistent with the assigned structure.

Provenance & Evidence