1-Diethoxyphosphorylpropan-2-one → Diethyl [8-(2-chloro-4-methoxyphenoxy)-2-oxooctan-3-yl]phosphonate

HRID 1855979Notes

Reaction equation

HRID 1855979 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:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]I>>[C:4]([CH:3]([P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:17]1[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:16]=1[Cl:15])(=[O:5])[CH3:6]

Participants

4

Reactant 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 62714Lithium hydrideHCID 18921928HCID 18921928, compound

Product 1

HCID 5271396Diethyl [8-(2-chloro-4-methoxyphenoxy)-2-oxooctan-3-yl]phosphonateYield 16.9%

Procedure

[II; Ar is 2-Cl-4-CH3OC6H3, Y is O(CH2)5, R is C2H5, R' is CH3CO] was prepared from 0.71 g of lithium hydride, 17.2 g of diethyl acetonylphosphonate and 34 g of 5-(2-chloro-4-methoxyphenoxy)pentyl 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 6.3 g of diethyl [1-acetyl-6-(2-chloro-4-methoxyphenoxy)hexyl]phosphonate as a light yellow oil; MIC vs. herpes simplex type 2=6 mcg/ml. The IR spectrum was 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-298edc40d67049449968a0fb3b5820a5
Source dataset
uspto-grants-1980_08
Patent number
US04217346

Reaction notes

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