Water → HCID 54066355, compound

HRID 1758262Notes

Reaction equation

HRID 1758262 reaction equation
I[CH:2]([CH3:4])[CH3:3].[O:5]1[C:9]2[CH:10]=[C:11]([CH2:14][C:15]#[N:16])[CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6]1.[OH-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH:2]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]2[CH:7]=[CH:6][O:5][C:9]=2[CH:10]=1)[C:15]#[N:16])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 126007356-Benzofuranacetonitrile

Product 1

HCID 54066355HCID 54066355, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Iodopropane (6.5 g, 0.038 mol) was added to a well-stirred mixture of benzofuran-6-acetonitrile (3.0 g, 0.019 mol), tetrabutylammonium hydrogen sulphate (6.5 g, 0.019 mol), sodium hydroxide (47% w/w, 20 cm3, 0.037 mol), water (10 cm3) and dichloromethane (50 cm3), and the mixture was refluxed for 6 hr. with good stirring. The organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed. Toluene (15 cm3) was added to the residue, the mixture was filtered, and the solvent was removed. The residue was chromatographed on silica using toluene as eluant, to give α-isopropylbenzofuran-6-acetonitrile (1.62, 0.0081 mol, 42.6%) as an oil. (Found: C, 79.32; H, 6.22; N, 6.55. C13H13NO requires C, 78.36, H, 6.58; N, 7.03%) t.l.c./silica/toluene RF 0.38.

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. additionToluene (15 cm3) was added to the residue
  7. filtrationthe mixture was filtered
  8. customthe solvent was removed
  9. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-0dfbde7671db48dbb59306d752066a6f
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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