2-Norbornene → HCID 2756665, compound

HRID 1816077Notes

Reaction equation

HRID 1816077 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[CH3:8][SiH:9]([CH3:11])[Cl:10]>C1(C)C=CC=CC=1.[Pt]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[Si:9]([CH3:11])([CH3:8])[Cl:10]

Participants

5

Reactant 2

HCID 103522-NorborneneHCID 66108Chlorodimethylsilane

Product 1

HCID 2756665HCID 2756665, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Norbornene (141 g, 1.50 mol) is dissolved in toluene (100 ml) and heated to 80° C. After the addition of the platinum catalyst ([COD]PtCl2, 70 mg), dimethylchlorosilane (169 g, 1.8 mol) is slowly added dropwise within 60 min, and the temperature rises to 98° C. Heating is continued at 80° C. for a further 1 h. Excess silane, unconverted norbornene and the solvent are distilled off at atmospheric pressure. The residue is fractionally distilled using a membrane pump vacuum. 255 g (93%) of a colorless liquid having b.p. of 120° C./10 mbar are obtained. Purity 99.7% (assessed by GC (gas chromatography)).

Workup

  1. additionis slowly added dropwise within 60 min
  2. customrises to 98° C
  3. temperatureHeating
  4. distillationExcess silane, unconverted norbornene and the solvent are distilled off at atmospheric pressure
  5. distillationThe residue is fractionally distilled
  6. customare obtained

Sources & evidence

ORD record
ord-6f1e90bc5fdf46b5971e7360cf459f76
Source dataset
uspto-grants-2005_04
Patent number
US06881855B2

Reaction notes

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