Tetraethoxysilane → Cyclopentyl(triethoxy)silane

HRID 1424697Notes

Reaction equation

HRID 1424697 reaction equation
C(O[Si:4]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.[CH:14]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+]>COC(C)(C)C>[CH:14]1([Si:4]([O:5][CH2:6][CH3:7])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6517TetraethoxysilaneHCID 25517Ammonium ChlorideHCID 178419650HCID 178419650, compound

Product 1

HCID 16217491Cyclopentyl(triethoxy)silane

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

60 ml of dry t-butyl methyl ether and 14.0 gram (0.067 mole) of tetraethoxysilane were charged in a 250 ml flask equipped with a reflux condenser and a stirring apparatus in an atmosphere of nitrogen and the solution of cyclopentyl magnesium bromide prepared above under (a) was slowly added while keeping the internal temperature below 10° C. After completion of addition stirring was carried out at room temperature for 6 hours and at reflux temperature for 2 hours. To the resulting reaction mass 10-20 ml of saturated aqueous ammonium chloride solution was added drop wise to dissolve magnesium salt. The organic layer was separated from the aqueous layer, dried and evaporated to give crude cyclopentyltriethoxysilane. The crude was purified by fractional distillation under reduced pressure, yielding 12 gram of pure cyclopentyltriethoxysilane (76% of the theoretical maximum yield based on the amount of tetraethoxysilane).

Workup

  1. customequipped with a reflux condenser
  2. additionwas slowly added
  3. customthe internal temperature below 10° C
  4. additionAfter completion of addition
  5. temperatureat reflux temperature for 2 hours
  6. additionwas added drop wise
  7. customThe organic layer was separated from the aqueous layer
  8. customdried
  9. customevaporated
  10. customto give crude cyclopentyltriethoxysilane
  11. distillationThe crude was purified by fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-28d1341b6ee944a5a8a43f387b831c2a
Source dataset
uspto-grants-2015_01
Patent number
US08927753B2

Reaction notes

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