Vinyltriethoxysilane → Phosphonic acid, P-(2-(triethoxysilyl)ethyl)-, diethyl ester

HRID 1829950

Reaction equation

HRID 1829950 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH:9]([Si:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH2:10]>>[Si:11]([CH2:9][CH2:10][P:1]([O:5][CH2:6][CH3:7])([O:2][CH2:3][CH3:4])=[O:8])([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 6516VinyltriethoxysilaneHCID 3780918Diethylphosphite

Product 1

HCID 69792Phosphonic acid, P-(2-(triethoxysilyl)ethyl)-, diethyl esterYield 33%

Procedure

Compounds of Formula II can be synthesised via a free radical promoted addition of a dialkyl phosphite to vinyl trialkoxy silane and then distillation, according to the procedure of G. H. Barnes and M. P. David in J. Org. Chem., 25, 1191, (1960). In this paper Barnes and David reported the synthesis of a number of organosilicon phosphonate esters and acids. They utilised known procedures for the free radical addition of dialkyl phosphites to double bonds. The state of this art is described in Org. Reactions. Vol. 13, 218–222. They reacted diethyl phosphite with vinyl triethoxy silane at 120–130° C. in the presence of a free radical initiator. The desired product, (EtO)3SiCH2CH2PO(OEt)2, was obtained after careful distillation in 33% yield.

Workup

  1. distillationdistillation
  2. customthe synthesis of a number of organosilicon phosphonate esters and acids

Sources & evidence

ORD record
ord-2169ac47b2d64c30858d3ea05b59ffcf
Source dataset
uspto-grants-2006_06
Patent number
US07064226B2

Linked notes

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