Sodium Chloride → Bis(3-phenylpropyl)(prop-2-en-1-yl)silane

HRID 547245Notes

Reaction equation

HRID 547245 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:12]([SiH:15](Cl)Cl)[CH:13]=[CH2:14].[Na+].[Cl-]>C(OCC)C>[CH2:12]([SiH:15]([CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 12503(3-Bromopropyl)benzeneHCID 77536Dichloro(prop-2-enyl)silaneHCID 5462224Magnesium

Product 1

HCID 71350844Bis(3-phenylpropyl)(prop-2-en-1-yl)silaneYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 500 mL Schlenk flask containing magnesium turnings (2.71 g, 111.5 mmol) in diethyl ether (250 mL) was added dropwise a solution of 1-bromo-3-phenylpropane (20.0 g, 100.5 mmol) over 4 hours. The resulting pale yellow solution was stirred for 10 hours at room temperature then cooled to 0° C. and treated with allyldichlorosilane (7.085 g, 50 mmol) via syringe. The resulting white slurry was stirred for 4 hours at room temperature then heated to reflux for 20 minutes. After filtration and aqueous work-up, the solvent was removed in vacuo to give a colorless liquid. Yield: 86%. FTIR (NaCl, cm−1): 3083, 3066, 3021, 2927, 2842, 2069, 1598, 1569, 1488, 1456, 1142, 1067, 1025, 987, 920, 891, 834, 745, 701. 1H NMR (CDCl3): 7.28, 7.17, 5.74, 4.89, 4.54, 3.74, 2.62, 1.67, 0.64.

Workup

  1. temperaturethen cooled to 0° C.
  2. stirringThe resulting white slurry was stirred for 4 hours at room temperature
  3. temperaturethen heated
  4. temperatureto reflux for 20 minutes
  5. filtrationAfter filtration and aqueous work-up
  6. customthe solvent was removed in vacuo
  7. customto give a colorless liquid

Sources & evidence

ORD record
ord-88b6cf63471d42fdb2cda3d35054561d
Source dataset
uspto-grants-2011_05
Patent number
US07939337B2

Reaction notes

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