1-Hexene → Silane, triethyl(1Z)-1-hexenyl-

HRID 1963755Notes

Reaction equation

HRID 1963755 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[SiH:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9]>N1C=CC=CC=1C1C(C2C=CC=CN=2)=CC=CN=1.C[Si](C[Fe]C[Si](C)(C)C)(C)C.C1(C)C=CC=CC=1>[Si:7]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6])([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 115971-HexeneHCID 12052Triethylsilane

Product 1

HCID 598073Silane, triethyl(1Z)-1-hexenyl-Yield 5%

Reagents, catalysts & solvents 2

HCID 178504291HCID 178504291, compoundCatalystHCID 1140TolueneSolvent

Procedure

A stock solution containing 5 mg of bis[(trimethylsilyl)methyl]iron(II) terpyridine and 0.60 g of toluene was charged into a scintillation vial in a nitrogen filled drybox. The toluene was removed in vacuo followed by addition of 0.114 g (1.4 mmol) of 1-hexene. To the same vial, 0.105 g (0.90 mmol) of Et3SiH was added. The vial was sealed with a small amount Krytox grease and electrical tape, removed from the drybox and placed in a 95° C. oil bath. The concentration of the iron complex was less than 0.1 mol % relative to the silane, and the reaction time was 4 hours to achieve greater than 90% conversion to (CH3CH2)3Si—(CH2)5—CH3. Less than 5% each of (CH3CH2)3Si—CH═CH—(CH2)3—CH3 and (CH3CH2)2(H)Si—(CH2)5—CH3 were formed.

Workup

  1. additionwas charged into a scintillation vial in a nitrogen filled drybox
  2. customThe toluene was removed in vacuo
  3. customremoved from the drybox
  4. customplaced in a 95° C.

Sources & evidence

ORD record
ord-3cbbb486c92c46b89cffce411bae86de
Source dataset
uspto-grants-2013_04
Patent number
US08415443B2

Reaction notes

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