Water → HCID 54066355, 화합물

HRID 1758262노트

반응식

HRID 1758262 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 54066355HCID 54066355, 화합물수율 42.6%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0dfbde7671db48dbb59306d752066a6f
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04372970

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