Methyl triflate → Trimethoxysilylpropyltrimethylammonium trifluoromethanesulfonate

HRID 537717Notes

Reaction equation

HRID 537717 reaction equation
[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])([O:6][CH3:7])[O:4][CH3:5].[F:14][C:15]([F:22])([F:21])[S:16]([O:19]C)(=[O:18])=[O:17]>C(OCC)(=O)C>[F:14][C:15]([F:22])([F:21])[S:16]([O-:19])(=[O:18])=[O:17].[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][N+:11]([CH3:15])([CH3:13])[CH3:12])([O:4][CH3:5])[O:6][CH3:7]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 756681-Propanamine, N,N-dimethyl-3-(trimethoxysilyl)-

Product 1

HCID 86654381Trimethoxysilylpropyltrimethylammonium trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.0 g of trimethoxysilylpropyldimethylamine and 18 g of ethyl acetate were charged into a 100 mL flask to be dissolved. While stirring the resultant mixed solution with a magnetic stirrer, to the mixed solution, a solution in which 5.9 g of methyl trifluoromethanesulfonate was dissolved in 24 g of ethyl acetate was gradually added at room temperature in a nitrogen atmosphere. The reaction mixture was refluxed over 3 days and therefrom, ethyl acetate was distilled off under reduced pressure. The resultant concentrate was dropped into 100 mL of diethyl ether and therefrom, trimethoxysilylpropyldimethyl amine and methyl trifluoromethanesulfonate as by-products were removed. This purification was repeated three times and then remaining diethyl ether was distilled off under reduced pressure, followed by dissolving the resultant concentrate in methanol to obtain a 30% methanol solution of trimethoxysilylpropyltrimethylammonium trifluoromethanesulfonate.

Workup

  1. dissolutionto be dissolved
  2. additionmixed solution with a magnetic stirrer
  3. additionwas gradually added at room temperature in a nitrogen atmosphere
  4. temperatureThe reaction mixture was refluxed over 3 days
  5. distillationethyl acetate was distilled off under reduced pressure
  6. concentrationThe resultant concentrate
  7. additionwas dropped into 100 mL of diethyl ether
  8. customtrimethoxysilylpropyldimethyl amine and methyl trifluoromethanesulfonate as by-products were removed
  9. customThis purification
  10. distillationremaining diethyl ether was distilled off under reduced pressure
  11. dissolutionby dissolving the resultant
  12. concentrationconcentrate in methanol

Sources & evidence

ORD record
ord-58a825e469604dd680d502c2220d5c5e
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

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