Trimethylsilyl iodide → Bistrimethylsilyl-3-cyanopropylphosphonate

HRID 1155181Notes

Reaction equation

HRID 1155181 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])(=[O:8])[O:5]CC)C.[CH3:14][Si:15](I)([CH3:17])[CH3:16]>C(Cl)(Cl)(Cl)Cl>[CH3:14][Si:15]([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]#[N:13])(=[O:8])[O:5][Si:15]([CH3:17])([CH3:16])[CH3:14])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 2526874-Diethoxyphosphorylbutanenitrile

Product 1

HCID 20562954Bistrimethylsilyl-3-cyanopropylphosphonate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

In an experiment to demonstrate this method, 4.0 g of diethyl-3-cyanopropylphosphonate in 12 ml of carbon tetrachloride, was treated with 5.6 ml of trimethylsilyl iodide. This was cooled to 0° C. and stirred for ten minutes, and allowed to warm to room temperature, forming bis(trimethylsilyl)-3-cyanopropylphosphonate.

Workup

  1. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-730bd60a21a148278b07a80ebc00947c
Source dataset
uspto-grants-1981_11
Patent number
US04299943

Reaction notes

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