1,7-Octadiene → Octane-1,8-diylbis(chlorodimethylsilane)

HRID 1492128Notes

Reaction equation

HRID 1492128 reaction equation
[CH3:1][SiH:2]([CH3:4])[Cl:3].[CH2:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]>C(Cl)Cl.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[Cl:3][Si:2]([CH3:4])([CH3:1])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:2]([Cl:3])([CH3:4])[CH3:1]

Participants

5

Reactant 2

HCID 194601,7-OctadieneHCID 66108Chlorodimethylsilane

Product 1

HCID 78770Octane-1,8-diylbis(chlorodimethylsilane)Yield 60%

Reagents, catalysts & solvents 2

HCID 11147318Tetrabutylammonium hexachloroplatinate(IV)CatalystHCID 6344DichloromethaneSolvent

Procedure

Dimethylchlorosilane (6.8 mL, 60 mmol) in CH2Cl2 (10 mL) was added by dropping funnel over 10 minutes to a mixture of 1,7-octadiene (4.5 mL, 30 mmol) and bis(tetrabutylammonium)hexachloroplatinate (272 mg, 0.3 mmol). After 3 hours at room temperature, the solvent was removed in vacuo and the residue taken up in pentane. The majority of the catalyst was removed by filtration under nitrogen and the filtrate was concentrated in vacuo to provide as an oily liquid 1,8 bis(chlorodimethyl silyl) octane 1H NMR (200 MHz, CDCl3)δ 1.94-1.75 (m,10H), 0.80 (t,4H), 0.40 (s.12H).

Workup

  1. customover 10 minutes
  2. customthe solvent was removed in vacuo
  3. customThe majority of the catalyst was removed by filtration under nitrogen
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8f2aa5c712ef4f898c6452eb81ac006e
Source dataset
uspto-grants-1994_12
Patent number
US05372980

Reaction notes

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