Water → HCID 54066355、化合物

HRID 1758262ノート

反応式

HRID 1758262 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 54066355HCID 54066355、化合物収率 42.6%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0dfbde7671db48dbb59306d752066a6f
出典データセット
uspto-grants-1983_02
特許番号
US04372970

反応ノート

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