1-Octene → HCID 131735857, compound

HRID 2206319Notes

Reaction equation

HRID 2206319 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[SiH:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11]>>[CH2:10]([Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:1][CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:11]

Participants

3

Reactant 2

HCID 81251-OcteneHCID 12052Triethylsilane

Product 1

HCID 131735857HCID 131735857, compound

Conditions

Temperature
23 °C

Procedure

In a nitrogen-filled drybox, a scintillation vial was charged with 0.100 g (0.891 mmol) of 1-octene and 0.449 mmol (0.5 equiv) of 0.052 g Et3SiH. 0.001 g (0.002 mmol, 0.5 mol %) of (MesPDI)CoMe was then added to the mixture and the reaction was stirred at room temperature (23° C.) for 24 hours. The reaction was quenched by exposure to air, and the product mixture was analyzed by gas chromatography and 1H and 13C NMR spectroscopy. Conversion of the SiH and olefin functional groups was greater than 99%. GC analysis showed 46% of the alkenylsilane and 52% octane. Both E and Z isomers of 1-triethylsilyl-2-octene were formed. The alkenylsilane product was purified by passing the mixture through a silica gel column with hexane followed by removal of the volatiles in vacuo. In another experiment, during which the progress of the reaction was monitored by NMR, 37% conversion occurred in 30 minutes at 23° C. Product distribution at that point was 36% E isomer, 21% Z isomer and 41% octane. The 1H and 13C NMR details of 1-triethylsilyl-2-octene are presented below.

Workup

  1. additionIn a nitrogen-filled drybox
  2. addition0.001 g (0.002 mmol, 0.5 mol %) of (MesPDI)CoMe was then added to the mixture
  3. customThe reaction was quenched by exposure to air

Sources & evidence

ORD record
ord-3af23a0596644edc85f61fea48ac480f
Source dataset
uspto-grants-2016_06
Patent number
US09371339B2

Reaction notes

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