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

HRID 1855981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855981
[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]

Komponenten

4

Edukt 3

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

Produkt 1

HCID 5271397Diethyl [9-(2-chloro-4-methoxyphenoxy)-2-oxononan-3-yl]phosphonateAusbeute 19,3 %

Versuchsvorschrift

[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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-234def41c7cb449fbdfa0af81208af9d
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04217346

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