Tetramethoxysilane → (3-(Triallylsilyl)propyl}dimethoxysilane

HRID 589223Notes

Reaction equation

HRID 589223 reaction equation
[CH3:1][O:2][Si:3](OC)(OC)[O:4][CH3:5].[CH2:10]([Si:13]([CH2:22][CH:23]=[CH2:24])([CH2:19][CH:20]=[CH2:21])[CH2:14][CH2:15][CH2:16][Mg]Br)[CH:11]=[CH2:12]>C(OCC)C>[CH2:19]([Si:13]([CH2:10][CH:11]=[CH2:12])([CH2:14][CH:15]=[CH2:16])[CH2:22][CH2:23][CH2:24][SiH:3]([O:4][CH3:5])[O:2][CH3:1])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 12682TetramethoxysilaneHCID 178460902HCID 178460902, compound

Product 1

HCID 131734459(3-(Triallylsilyl)propyl}dimethoxysilaneYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, tetramethoxysilane (5) (0.482 ml, 3.268 mmol) was cooled down to 0° C., then diethyl ether solution of 10 ml (7.2 mmol) of 0.72M 3-(triallylsilyl)propylmagnesium bromide (24) was added dropwise, then stirred at room temperature for 15 hours. The reacted mixture was cooled down to 0° C., quenched with water, then saturated ammonium chloride aqueous solution was added until the salt was completely dissolved. The obtained organic layer was separated, and the obtained water layer was extracted with diethyl ether, the collected organic layer was each washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, obtaining a crude product. The crude product was purified through short silica gel column chromatography (eluent: hexane/ethyl acetate=20/1), obtaining bis {(3-(triallylsilyl)propyl}dimethoxysilane (29′) represented by the following chemical reaction equation (yield: 1.04 g, yield (%): 67%).

Workup

  1. temperatureThe reacted mixture was cooled down to 0° C.
  2. customquenched with water
  3. additionsaturated ammonium chloride aqueous solution was added until the salt
  4. dissolutionwas completely dissolved
  5. customThe obtained organic layer was separated
  6. extractionthe obtained water layer was extracted with diethyl ether
  7. washeach washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customobtaining a crude product
  12. customThe crude product was purified through short silica gel column chromatography (eluent: hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-a889595d4bdd46f8a222d1beb30fcd31
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

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