Styrene → Phenethylmethyldiethoxysilane

HRID 1873088Notes

Reaction equation

HRID 1873088 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][SiH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>[Pt].C1(C)C=CC=CC=1>[CH2:1]([CH2:9][SiH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7501Styrene3×HCID 74848Methyldiethoxysilane2×

Product 1

HCID 123960403PhenethylmethyldiethoxysilaneYield 63%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Comparative Example 5. The platinum-catalyzed reaction of styrene and methyldiethoxysilane in the absence of a hydro(acyloxy)silane compound. A 212 mg sample of styrene (2 mmoles) and 279 mg of methyldiethoxysilane (HSi(CH3)(OEt)2, 2.1 mmoles) were placed in a glass reaction tube. This was followed by the addition of 0.001 mL of a toluene solution (platinum content=0.4 wt %) of a zero-valent platinum complex with divinylsiloxane. The reaction tube was subsequently sealed with Teflon™ tape, placed in an oil bath heated to 80° C., and heated for 1 hour. After cooling, analysis of the contents by gas chromatography showed an approximately 65% conversion of the vinyl group in the styrene. The hydrosilylate yield was 63% phenethylmethyldiethoxysilane. The α-phenethyl adduct: β-phenethyl adduct ratio was 1:1.65.

Workup

  1. customplaced in an oil bath
  2. temperatureheated for 1 hour
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-58be669e56d24e98ad49d230594d2f9b
Source dataset
uspto-grants-2000_08
Patent number
US06111126

Reaction notes

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