Aniline → [2-(Bicyclo[2.2.1]hept-5-en-2-yl)ethyl](trimethoxy)silane

HRID 2406913Notes

Reaction equation

HRID 2406913 reaction equation
[CH:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)=[CH2:2].NC1C=CC=CC=1.[CH3:17][O:18][SiH:19]([O:22][CH3:23])[O:20][CH3:21]>[Pt]>[CH:4]12[CH2:9][CH:7]([CH:6]=[CH:5]1)[CH2:8][CH:3]2[CH2:1][CH2:2][Si:19]([O:22][CH3:23])([O:20][CH3:21])[O:18][CH3:17]

Participants

5

Reactant 3

HCID 6115AnilineHCID 17215TrimethoxysilaneHCID 182735-Vinyl-2-norbornene

Product 1

HCID 22388779[2-(Bicyclo[2.2.1]hept-5-en-2-yl)ethyl](trimethoxy)silane

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Conditions

Temperature
100 °C

Procedure

Into a 5 liter round bottom flask, fitted with an addition funnel, Friedrich condenser, thermocouple, stir bar and nitrogen line, were charged 5-vinyl-2-norbornene (1500 grams, 12.48 moles, from Sigma-Aldrich), platinum catalyst (4.5 grams of a 3 wt % solution of platinum(0)-1,3-divinyl-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in xylenes) and aniline (2.87 grams, 0.031 moles). The reaction mixture was heated gently to 100° C. and then trimethoxysilane (1372.5 grams, 11.23 moles from Momentive Performance Materials, Inc.) was incrementally charged into the flask. The reaction temperature was maintained using (controlling) the rate of addition and heating. The reaction mixture temperature was maintained in a ranged of from 63° C. to 118° C. The mixture was recatalyzed with an additional 1.3 grams of Pt complex and house air was bubbled intermittently into the reaction mixture using a small gage stainless steel needle introduced through a rubber septum. After all the trimethoxysilane had been consumed, the mixture was purified by vacuum distillation. The mono trimethoxysilylated product was isolated at 93° C. and 3 mmHg pressure leaving behind the his trimethoxysilylated constituent.

Workup

  1. customInto a 5 liter round bottom flask, fitted with an addition funnel
  2. temperatureThe reaction temperature was maintained
  3. additionthe rate of addition
  4. temperatureheating
  5. temperatureThe reaction mixture temperature was maintained in
  6. customa ranged of from 63° C. to 118° C
  7. customwas bubbled intermittently into the reaction mixture
  8. additionintroduced through a rubber septum
  9. customAfter all the trimethoxysilane had been consumed
  10. distillationthe mixture was purified by vacuum distillation
  11. customwas isolated at 93° C.
  12. custom3 mmHg pressure leaving behind the his trimethoxysilylated constituent

Sources & evidence

ORD record
ord-c8116948442f4aec929ff6d8c971e174
Source dataset
uspto-grants-2014_08
Patent number
US08809479B2

Reaction notes

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