1-Diethoxyphosphorylpropan-2-one → Diethyl [9-(2-chloro-4-methoxyphenoxy)-2-oxononan-3-yl]phosphonate

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Reaction Steps

[II; Ar is 2-Cl-4-CH3OC6H3, Y is O(CH2)6, R is C2H5, R' is CH3CO] was prepared from 0.47 g of lithium hydride, 11.6 g of diethyl acetonylphosphonate and 22 g of 6-(2-chloro-4-methoxyphenoxy)hexyl iodide according to the procedure of Example 2(b). The product was chromatographed on Florisil and further purified by preparative TLC on silica gel to give 5.0 g of diethyl [1-acetyl-7-(2-chloro-4-methoxyphenoxy)heptyl]phosphonate as a yellow oil; MIC vs. herpes simplex type 2=6 mcg/ml. The IR and NMR spectra were consistent with the assigned structure.

Provenance & Evidence