2-Thiophenecarboxylic acid → Acetylthiomethyltriethoxysilane

HRID 396929

Reaction equation

HRID 396929 reaction equation
[S:1]1[CH:5]=[CH:4]C=[C:2]1C(O)=O.[O-:9]CC.[Na+].S1C=CC=C1CC(O)=O.ClC[Si:24]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>COCCOCCOC>[C:5]([S:1][CH2:2][Si:24]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])(=[O:9])[CH3:4]

Participants

6

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 159702-Thiopheneacetic acidHCID 84858Silane, (chloromethyl)triethoxy-HCID 2723922Sodium ethoxide

Product 1

HCID 12135714AcetylthiomethyltriethoxysilaneYield 55%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
8 °C

Procedure

This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using a nonprotic solvent. 88 grams of powdered sodium ethoxide and 600 ml diglyme were charged into a one-liter, three-neck round bottomed flask equipped with magnetic stir bar, temperature probe/controller, heating mantle, addition funnel, condenser, N2 inlet, and ice water bath. The solution was cooled to 8° C., and 105 grams of thiolacetic acid was added slowly via the addition funnel, keeping the temperature below 60° C. The solution was allowed to cool to 35° C., and 250 grams of chloromethyltriethoxysilane was added via the addition funnel. After addition was complete, the solution was heated to 70° C., where a brief exotherm to 120° C. was observed. The solution was heated at 70° C. for an additional three hours. A white solid formed which was filtered first through a 0.1 μm pressure filter and then a 0.01 μm filter to give a clear, black solution. The solvent was removed under reduced pressure, and the remaining liquid vacuum distilled to yield 163 grams of a clear and colorless liquid, a 55 percent yield.

Workup

  1. customequipped with magnetic stir bar
  2. temperaturetemperature probe/controller, heating mantle
  3. additionaddition funnel, condenser, N2 inlet, and ice water bath
  4. customthe temperature below 60° C
  5. temperatureto cool to 35° C.
  6. additionAfter addition
  7. temperaturethe solution was heated to 70° C.
  8. customto 120° C.
  9. temperatureThe solution was heated at 70° C. for an additional three hours
  10. customA white solid formed which
  11. filtrationwas filtered first through a 0.1 μm pressure
  12. filtrationfilter
  13. filtrationa 0.01 μm filter
  14. customto give a clear, black solution
  15. customThe solvent was removed under reduced pressure
  16. distillationthe remaining liquid vacuum distilled
  17. customto yield 163 grams of a clear and colorless liquid

Sources & evidence

ORD record
ord-ce850b0c132b4594a4b26de67431649d
Source dataset
uspto-grants-2003_08
Patent number
US06608125B2

Linked notes

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