Acetonitrile → Benzonitrile, 4-[1-[(trimethylsilyl)methyl]ethenyl]-

HRID 368914Notes

Reaction equation

HRID 368914 reaction equation
O([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)S(C(F)(F)F)(=O)=O.[CH2:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+].C(#N)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].O>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:18](=[CH2:19])[CH2:17][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:10][CH:11]=1)#[N:16]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 69808AllyltrimethylsilaneHCID 5501824-Cyanophenyl trifluoromethanesulfonate

Product 1

HCID 10727431Benzonitrile, 4-[1-[(trimethylsilyl)methyl]ethenyl]-Yield 54%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent

Procedure

Table 1, Entry 8. In the reaction tube were mixed 4-cyanophenyl triflate (0.251 g,1.0 mmol), allyltrimethylsilane (0.571 g, 5.0 mmol), palladium acetate (0.00673 g, 0.030 mmol), DPPF (0.0366 g, 0.066 mmol), potassium carbonate (0.207 g, 1.5 mmol) and 1.0 ml acetonitrile.under nitrogen. The contents of the flask were irradiated for 5.00 min with an effect of 50 W. After cooling, the product mixture was poured into 25 ml water and was extracted three times with 25 ml diethyl ether. The combined extracts were washed two times with 25 ml saline and concentrated to an oil. The crude product was purified by repeated Kugelrohr distillation. The yield was 54% (clear oil).

Workup

  1. customThe contents of the flask were irradiated for 5.00 min with an effect of 50 W
  2. temperatureAfter cooling
  3. extractionwas extracted three times with 25 ml diethyl ether
  4. washThe combined extracts were washed two times with 25 ml saline
  5. concentrationconcentrated to an oil
  6. customThe crude product was purified
  7. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-91b4d7b83a464010a1435615e0c99d05
Source dataset
uspto-grants-2000_10
Patent number
US06136157

Reaction notes

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