Toluene → HCID 101765612, compound

HRID 2220005Notes

Reaction equation

HRID 2220005 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[CH3:20][SiH:21]([CH3:26])[O:22][SiH:23]([CH3:25])[CH3:24].[C:27]1(C)C=CC=CC=1>>[CH3:20][Si:21]([CH2:27][CH2:4][CH2:3][CH2:2][CH2:1][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)([CH3:26])[O:22][SiH:23]([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 1140TolueneHCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 17980967HCID 17980967, compound

Product 1

HCID 101765612HCID 101765612, compoundYield 84%

Procedure

8.12 g (0.032 mol) of 4′-But-3-enyloxy-biphenyl-4-carbonitrile is dissolved in 80 mL of dry toluene and 21.50 g (0.16 mol) of 1,1,3,3-Tetramethyl-disiloxane is added. Dry air bubbled through the solution for 2 min and few drops of platinium(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in xylene are added. After stirring at room temperature for 20 h with exclusion of moisture, the solvent and excess of 1,1,3,3-Tetramethyl-disiloxane are distilled off under reduced pressure. The residue purified by column chromatography on silica gel using a mixture of CH2Cl2/pentane (75/25) as eluent gives a colourless oil (10.67 g, 84% yield).

Workup

  1. customDry air
  2. custombubbled through the solution for 2 min
  3. additionfew drops of platinium(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in xylene are added
  4. distillationthe solvent and excess of 1,1,3,3-Tetramethyl-disiloxane are distilled off under reduced pressure
  5. customThe residue purified by column chromatography on silica gel using
  6. additiona mixture of CH2Cl2/pentane (75/25) as eluent

Sources & evidence

ORD record
ord-f154932fa29348efa60f28cc7134efa5
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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