Trimethylsilyl cyanide → HCID 13511740, compound

HRID 254482Notes

Reaction equation

HRID 254482 reaction equation
C[Si]([C:5]#[N:6])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH:26]([C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[CH2:27][CH3:28]>C(#N)C>[C:32]1([CH3:35])[CH:33]=[CH:34][C:29]([CH:26]([CH2:27][CH3:28])[C:5]#[N:6])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 19743036HCID 19743036, compound

Product 1

HCID 13511740HCID 13511740, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.36 g (74.4 mmol) Trimethylsilyl cyanide was added to a solution of 74.4 ml (1.0 M in THF, 74.4 mmol) tetrabutylammonium flouride in 300 ml acetonitrile and the mixture was stirred for 5 minutes. 5.28 g (24.8 mmol) rac-1-(1-Bromo-propyl)-4-methylbenzene were added and the reaction mixture was stirred at ambient temperature for 16 hours. The solvent was removed in vacuo and the viscous residue obtained was partitioned between water and dichloromethane. The dichloromethane was separated, then washed with water, dried over MgSO4 and evaporated to dryness. Purification of the residue by column chromatography on silica gel with a gradient of heptane to 9:1 heptane/ethyl acetate afforded rac-2-p-tolyl-butyronitrile as a colourless oil. NMR (CDCl3, ppm): 0.95 (3H, t), 1.77 (2H, m), 2.21 (3H, s), 3.58 (1H, t), 7.07 (4H, m).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 16 hours
  2. customThe solvent was removed in vacuo
  3. customthe viscous residue obtained
  4. customwas partitioned between water and dichloromethane
  5. customThe dichloromethane was separated
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness
  9. customPurification of the residue by column chromatography on silica gel with a gradient of heptane to 9:1 heptane/ethyl acetate

Sources & evidence

ORD record
ord-932c2ebba1fa4b0bbbd13b6fc4a78aa6
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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