Hydrochloric Acid → Bis{3-(triallylsilyl)propyl}(methoxy)methylsilane

HRID 589227Notes

Reaction equation

HRID 589227 reaction equation
[CH3:1][O:2][C:3]([SiH3:8])(OC)OC.C(O[CH2:12][CH3:13])C.[CH2:14]([Si:17]([CH2:26][CH:27]=[CH2:28])([CH2:23][CH:24]=[CH2:25])[CH2:18][CH2:19][CH2:20][Mg]Br)[CH:15]=[CH2:16].Cl>O>[CH2:14]([Si:17]([CH2:26][CH:12]=[CH2:13])([CH2:18][CH:19]=[CH2:20])[CH2:23][CH2:24][CH2:25][SiH:8]([CH2:20][CH2:19][CH2:18][Si:17]([CH2:26][CH:27]=[CH2:28])([CH2:14][CH:15]=[CH2:16])[CH2:23][CH:24]=[CH2:25])[CH2:3][O:2][CH3:1])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 101924291Trimethoxymethyl silaneHCID 178460902HCID 178460902, compound

Product 1

HCID 131734460Bis{3-(triallylsilyl)propyl}(methoxy)methylsilaneYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, trimethoxymethylsilane (18) (42 μl, 0.3 mmol) was added into a reaction container, cooled down to 0° C. and then diethyl ether solution of 0.9M 3-(triallylsilyl)propylmagnesium bromide (24) (1 mL, 0.9 mmol) was dropped. After dropping, stirring was continued at room temperature for 5 hours. To the reacted mixture, water was added to stop the reaction, then 10% hydrochloric acid 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 washed each with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order, then dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, obtaining bis{3-(triallylsilyl)propyl}(methoxy)methylsilane (35) represented by the following chemical reaction equation (yield: 85 mg, yield (%): 62%).

Workup

  1. customthe reaction
  2. dissolutionwas completely dissolved
  3. customThe obtained organic layer was separated
  4. extractionthe obtained water layer was extracted with diethyl ether
  5. washThe collected organic layer was washed each with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7880462910c048e7bddbc15f0f4a2f52
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

Loading…