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

HRID 1855981Notes

Reaction equation

HRID 1855981 reaction equation
[H-].[Li+].[CH2:3]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[C:4]([CH3:6])=[O:5].[Cl:15][C:16]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]I>>[C:4]([CH:3]([P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:17]1[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:16]=1[Cl:15])(=[O:5])[CH3:6]

Participants

4

Reactant 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 62714Lithium hydrideHCID 12363405HCID 12363405, compound

Product 1

HCID 5271397Diethyl [9-(2-chloro-4-methoxyphenoxy)-2-oxononan-3-yl]phosphonateYield 19.3%

Procedure

[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.

Workup

  1. customThe product was chromatographed on Florisil
  2. customfurther purified by preparative TLC on silica gel

Sources & evidence

ORD record
ord-234def41c7cb449fbdfa0af81208af9d
Source dataset
uspto-grants-1980_08
Patent number
US04217346

Reaction notes

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