1-Diethoxyphosphorylpropan-2-one → Phosphonic acid, (1-acetyl-5-(2-chloro-4-methoxyphenoxy)pentyl)-, diethyl ester

HRID 1855980Notes

Reaction equation

HRID 1855980 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:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22]I>>[C:4]([CH:3]([P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:17]1[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:16]=1[Cl:15])(=[O:5])[CH3:6]

Participants

4

Reactant 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 62714Lithium hydrideHCID 233473142-Chloro-1-(4-iodobutoxy)-4-methoxybenzene

Product 1

HCID 5271395Phosphonic acid, (1-acetyl-5-(2-chloro-4-methoxyphenoxy)pentyl)-, diethyl esterYield 15.9%

Procedure

[II; Ar is 2-Cl-4-CH3OC6H3, Y is O(CH2)4, R is C2H5, R' is CH3CO] was prepared from 0.79 g of lithium hydride, 19.4 g of diethyl acetonylphosphonate and 34.0 g of 4-(2-chloro-4-methoxyphenoxy)butyl iodide according to the procedure of Example 2(b). The product was chromatographed on Florisil to give 6.45 g of diethyl [1-acetyl-5-(2-chloro-4-methoxyphenoxy)pentyl]phosphonate as a yellow oil; MIC vs. herpes simplex type 2=12 mcg/ml. The NMR spectrum was consistent with the assigned structure.

Workup

  1. customThe product was chromatographed on Florisil

Sources & evidence

ORD record
ord-bf655c26e86d4bde8138c9556bd78ec2
Source dataset
uspto-grants-1980_08
Patent number
US04217346

Reaction notes

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