Sodium Iodide → 3-Iodopropyl-tris(trimethylsiloxy)silane

HRID 1478938Notes

Reaction equation

HRID 1478938 reaction equation
Cl[CH2:2][CH2:3][CH2:4][Si:5]([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[O:6][Si:7]([CH3:10])([CH3:9])[CH3:8].[I-:21].[Na+]>CC(C)=O>[I:21][CH2:2][CH2:3][CH2:4][Si:5]([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[O:6][Si:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 27578913-(3-Chloropropyl)-1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane

Product 1

HCID 223256933-Iodopropyl-tris(trimethylsiloxy)silaneYield 79.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

90 g of 3-chloropropyltris(trimethylsiloxy)silane (27) (Chem. Abstracts No. 18077-31-1) and 105.22 g of sodium iodide are added to 250 ml of acetone and stirred for 24 hours at reflux. The acetone is evaporated and the residue taken up in methylene chloride. The organic phase is washed with water, dried and evaporated. 89 g of the desired 3-iodopropyl-tris(trimethylsiloxy)silane (28) are obtained; 1H-NMR (ppm, CDCl3): 3.12 2H t, 1.75 2H txt, 0.43 2H t, 0 27H s.

Workup

  1. temperatureat reflux
  2. customThe acetone is evaporated
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-991fa046e4424002a203c0a700519931
Source dataset
uspto-grants-2016_08
Patent number
US09403987B2

Reaction notes

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