Toluene → HCID 131730139, compound

HRID 1799816Notes

Reaction equation

HRID 1799816 reaction equation
C([Ge:3](CC)(C=C)C=C)C.[C:10]([C:12]1([O:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)#[CH:11].[C:23]1([CH3:29])[CH:28]=[CH:27]C=[CH:25][CH:24]=1>>[CH2:24]([C:23]([CH2:28][CH3:27])=[CH:29][GeH2:3][C:11]#[C:10][C:12]1([O:18][Si:19]([CH3:20])([CH3:22])[CH3:21])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH3:25]

Participants

4

Reactant 3

HCID 1140TolueneHCID 552482Silane, [(1-ethynylcyclohexyl)oxy]trimethyl-HCID 12461332HCID 12461332, compound

Product 1

HCID 131730139HCID 131730139, compoundYield 55%

Procedure

As in reaction conditions of Example I, to 3.99 mL of toluene, the 0.04 g of carbonylchlorhydridebis(tricyclohexylphosphine)ruthenium(II) is added and the reaction was carried out between 1.02 g of diethyldivinylgermane and 0.54 g 1-ethynyl-1-(trimethylsiloxy)cyclohexane. Conversion of the terminal alkyne and raw product yield was 65%. In order to remove the catalyst from the system, the solvent and any residual unreacted reactants were evaporated from the post-reaction mixture and the whole material was transferred onto a chromatographic column filled with silica gel modified with a triethylamine, wherafter product was separated, using hexane as eluent. The product, 1-[{diethylvinylgermyl}ethynyl]-1-(trimethylsiloxy)cyclohexane, was obtained at a yield of 55%, in the form of an oily liquid with a light straw color. The product structure was confirmed by 1H, 13C NMR and GCMS analyses.

Workup

  1. customAs in reaction conditions of Example I
  2. customIn order to remove the catalyst from the system
  3. customthe solvent and any residual unreacted reactants were evaporated from the post-reaction mixture
  4. additionfilled with silica gel
  5. customwas separated

Sources & evidence

ORD record
ord-2c741290e2a94222a5f7f767678ec6af
Source dataset
uspto-grants-2013_01
Patent number
US08344169B2

Reaction notes

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