Methyl triflate → HCID 86654379, compound

HRID 537709Notes

Reaction equation

HRID 537709 reaction equation
[CH3:1][O:2][Si:3]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:6][CH3:7])[O:4][CH3:5].[F:16][C:17]([F:24])([F:23])[S:18]([O:21]C)(=[O:20])=[O:19]>C(OCC)(=O)C>[F:16][C:17]([F:24])([F:23])[S:18]([O-:21])(=[O:20])=[O:19].[CH3:1][O:2][Si:3]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N+:11]=1[CH3:17])([O:6][CH3:7])[O:4][CH3:5]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 27605062-(Trimethoxysilylethyl)pyridine

Product 1

HCID 86654379HCID 86654379, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.0 g of 2-(trimethoxysilylethyl)pyridine 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 5.4 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, 2-(trimethoxysilylethyl)pyridine 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 trimethoxysilylethylmethylpyridinium 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. custom2-(trimethoxysilylethyl)pyridine 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-411c087dd96247e2b633937c169ec524
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

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