Hydrochloric Acid → {3-(Triallylsilyl)propyl}(methoxy)dimethylsilane

HRID 589225Notes

Reaction equation

HRID 589225 reaction equation
[CH3:1][O:2][Si:3](OC)([CH3:5])[CH3:4].C(OCC)C.[CH2:13]([Si:16]([CH2:25][CH:26]=[CH2:27])([CH2:22][CH:23]=[CH2:24])[CH2:17][CH2:18][CH2:19][Mg]Br)[CH:14]=[CH2:15].Cl>O>[CH2:13]([Si:16]([CH2:25][CH:26]=[CH2:27])([CH2:22][CH:23]=[CH2:24])[CH2:17][CH2:18][CH2:19][Si:3]([O:2][CH3:1])([CH3:5])[CH3:4])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 66187DimethoxydimethylsilaneHCID 178460902HCID 178460902, compound

Product 1

HCID 86726597{3-(Triallylsilyl)propyl}(methoxy)dimethylsilaneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, dimethoxydimethylsilane (31) (1.0 ml, 7.0 mmol) was added to a reaction container, cooled down to 0° C., diethyl ether solution of 0.72M 3-(triallylsilyl)propylmagnesium bromide (24) (19.44 mL, 14 mmol) was added dropwise. After the dropwise adding, stirring was continued at room temperature for 5 hours. To the reaction 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, dried over anhydrous magnesium sulfate, then filtered, concentrated under reduced pressure, obtaining {3-(triallylsilyl)propyl}(methoxy)dimethylsilane (32) represented by the following chemical reaction equation (yield: 1.5 g, yield (%): 72%).

Workup

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

Sources & evidence

ORD record
ord-f1016c2e3f194fe49a9a49c06728a2d7
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

Loading…