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

HRID 1855978Notes

Reaction equation

HRID 1855978 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:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]I>>[C:4]([CH:3]([P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:17]1[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:16]=1[Cl:15])(=[O:5])[CH3:6]

Participants

4

Reactant 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 62714Lithium hydrideHCID 19378827HCID 19378827, compound

Product 1

HCID 5271398Phosphonic acid, (1-acetyl-8-(2-chloro-4-methoxyphenoxy)octyl)-, diethyl esterYield 18.4%

Procedure

[II; Ar is 2-Cl-4-CH3OC6H3, 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 2(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.

Workup

  1. customThe product was chromatographed on Florisil
  2. customfurther purified by preparative thin layer chromatography (TLC) on silica gel

Sources & evidence

ORD record
ord-0b1cc24edeca4d5cb171485a4782028e
Source dataset
uspto-grants-1980_08
Patent number
US04217346

Reaction notes

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