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

HRID 1758264노트

반응식

HRID 1758264 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 94433Tetrabutylammonium hydrogen sulfate촉매

실험 절차

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%).

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. customThe residue was chromatographed on silica

출처 및 근거

ORD 기록
ord-3350e400819548e4812fe8ee26de4671
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04372970

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