Tetrahydrothiophene → HCID 86654382, compound

HRID 537719Notes

Reaction equation

HRID 537719 reaction equation
[S:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][Si:8]([CH2:13][CH2:14][CH2:15][I:16])([O:11][CH3:12])[O:9][CH3:10]>C(OCC)(=O)C>[I-:16].[CH3:6][O:7][Si:8]([CH2:13][CH2:14][CH2:15][CH:2]1[CH2:3][CH2:4][CH2:5][S:1]1)([O:11][CH3:12])[O:9][CH3:10]

Participants

4

Reactant 2

HCID 1127TetrahydrothiopheneHCID 2759373(3-Iodopropyl)trimethoxysilane

Product 1

HCID 86654382HCID 86654382, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2.0 g of tetrahydrothiophene 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 9.9 g of trimethoxysilylpropyl iodide 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, tetrahydrothiophene and trimethoxysilylpropyl iodide 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 trimethoxysilylpropyltetrahydrothiophene iodide.

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. customtetrahydrothiophene and trimethoxysilylpropyl iodide 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-4982a9d530f347d7b9be9e693cedc2a8
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

Loading…