Silanol → Ethylnorbornene

HRID 258335

Reaction equation

HRID 258335 reaction equation
[SiH3]O.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:19]12([CH2:26][CH2:27][Si](C)(C)Cl)[CH2:25][CH:22]([CH:23]=[CH:24]1)[CH2:21][CH2:20]2>CO>[CH2:26]([C:19]12[CH2:25][CH:22]([CH2:23][CH2:24]1)[CH:21]=[CH:20]2)[CH3:27]

Participants

5

Reactant 3

HCID 142154SilanolHCID 22388891NorbornenylethyldimethylchlorosilaneHCID 69041942Triethylamine dimethylaminopyridine

Product 1

HCID 21867936Ethylnorbornene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Silanol fluid, Rhone Poulenc 48V3500, (0.092 eq OH) was stirred under nitrogen and warmed to 70° C. with triethylamine-dimethylaminopyridine (1.05 eq, 1% DMAP by weight). The product of example 2 (0.0956 eq, 20.5 g) was added. The reaction mixture was stirred at 75° C. for three hours then methanol (50 g) was added slowly. After one hour, volatiles were removed by concentration on a rotary evaporator, the reaction mixture was diluted with hexane and filtered through diatomaceous earth. Removal of solvent on a rotary evaporator at 75° C. (0.1 mm Hg) gave the product: Viscosity 4680 cps, GPC MWwt 30787, Mnumber 23943.

Workup

  1. waitAfter one hour
  2. customvolatiles were removed by concentration on a rotary evaporator
  3. additionthe reaction mixture was diluted with hexane
  4. filtrationfiltered through diatomaceous earth
  5. customRemoval of solvent
  6. customon a rotary evaporator at 75° C. (0.1 mm Hg)
  7. customgave the product

Sources & evidence

ORD record
ord-7890260ad9504312bbf8afdc2b15c8d4
Source dataset
uspto-grants-1993_11
Patent number
US05266670

Linked notes

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