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

HRID 1758264ノート

反応式

HRID 1758264 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 94433Tetrabutylammonium hydrogen sulfate触媒

実験手順

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%).

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. customThe residue was chromatographed on silica

出典と根拠

ORDレコード
ord-3350e400819548e4812fe8ee26de4671
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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