Ethylene glycol diallyl ether → 1-Trichlorosilanyl-3-[2-(3-trichlorosilanyl-propoxy)-ethoxy]-propane

HRID 2391754Notes

Reaction equation

HRID 2391754 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH:9]=[CH2:10])[CH:2]=[CH2:3].[Cl:11][SiH:12]([Cl:14])[Cl:13]>O.Cl.Cl.Cl[Pt](Cl)(Cl)Cl>[Cl:11][Si:12]([Cl:14])([Cl:13])[CH2:3][CH2:2][CH2:1][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][Si:12]([Cl:14])([Cl:13])[Cl:11]

Participants

4

Reactant 2

HCID 24151Ethylene glycol diallyl etherHCID 24811Trichlorosilane

Product 1

HCID 866504851-Trichlorosilanyl-3-[2-(3-trichlorosilanyl-propoxy)-ethoxy]-propaneYield 70%

Reagents, catalysts & solvents 1

HCID 16211507Platinate(2-), hexachloro-, hydrogen, hydrate (1:2:1), (OC-6-11)-Catalyst

Conditions

Temperature
80 °C

Procedure

3-(2-Allyloxy-ethoxy)-propene (20 g, 0.141 mol) and 40 mg of hydrogen hexachloroplatinate (IV) hydrate were added to a 250-mL air-free flask with a condenser. Trichlorosilane (40 mL, 0.396 mol) was added dropwise to the stirred solution which was subsequently heated in an oil bath of 80° C. The reaction mixture was heated at reflux for 4 hours and then distilled in vacuum. The fraction containing di(3-trichlorosilyl)propyl ethylene ether (39 g, 0.0944 mol) at 90° C. and 20 mtorr was collected with a yield of 70% based on 3-(2-allyloxy-ethoxy)-propene. 1H NMR (400 Mz, CDCl3): δ 1.5 (t, 2H), 1.8 (m, 2H), 3.4 (t, 2H), 3.6 (t, 2H). 29Si NMR (79.6 Mz, CDCl3): 13.4 (s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. distillationdistilled in vacuum
  4. custom20 mtorr was collected with a yield of 70%

Sources & evidence

ORD record
ord-7bf2e0af714c458584679f2053e35125
Source dataset
uspto-grants-2012_09
Patent number
US08274075B2

Reaction notes

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