Isopropyl iodide → alpha-Isopropylbenzo(b)thiophene-5-acetonitrile

HRID 1758264Notes

Reaction equation

HRID 1758264 reaction equation
I[CH:2]([CH3:4])[CH3:3].[S:5]1[CH:9]=[CH:8][C:7]2[CH:10]=[C:11]([CH2:14][C:15]#[N:16])[CH:12]=[CH:13][C:6]1=2.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH:2]([CH:14]([C:11]1[CH:12]=[CH:13][C:6]2[S:5][CH:9]=[CH:8][C:7]=2[CH:10]=1)[C:15]#[N:16])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 20509997(Benzo[b]thiophen-5-yl)acetonitrile

Product 1

HCID 20510017alpha-Isopropylbenzo(b)thiophene-5-acetonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

2-Iodopropane (5.10 g, 0.03 mol) was added to a well stirred mixture of benzo(b)thiophene-5-acetonitrile (2.62 g, 0.015 mol), tetrabutylammonium hydrogen sulphate (5.10 g, 0.015 mol), sodium hydroxide (47% w/w, 1.72 cm3, 0.03 mol) and the mixture was refluxed for 6 hr. with vigorous stirring. The organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed. The residue was chromatographed on silica using toluene as the eluant and the component with RF 0.52 was isolated as α-isopropylbenzo(b)thiophene-5-acetonitrile (2.00 g, 0.0093 mol, 61.9%).

Workup

  1. temperaturethe mixture was refluxed for 6 hr
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-3350e400819548e4812fe8ee26de4671
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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