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

HRID 1855981ノート

反応式

HRID 1855981 の反応式
[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]

参加物

4

反応物 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 62714Lithium hydrideHCID 12363405HCID 12363405、化合物

生成物 1

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

実験手順

[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.

後処理

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

出典と根拠

ORDレコード
ord-234def41c7cb449fbdfa0af81208af9d
出典データセット
uspto-grants-1980_08
特許番号
US04217346

反応ノート

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