Benzenesulfonyl chloride → 4-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-Indole

HRID 896289노트

반응식

HRID 896289 반응식
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>O1CCCC1.CCOC(C)=O>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23]

참가 물질

7

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 106317214-(2-chloroethoxy)-1H-indole

생성물 1

HCID 104047244-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-Indole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A stirred solution of 4-(2-chloroethoxy)-1H-indole (3.4 g, 17.4 mmol) in tetrahydrofuran is treated with sodium hydride (60% in mineral oil, 1.04 g, 26.1 mmol) under nitrogen at room temperature, stirred for 30 minutes, treated with benzenesulfonyl chloride (3.4 mL, 26.1 mmol) stirred at room temperature overnight and treated with saturated NaHCO3 and EtOAc. The resultant phases are separated. The aqueous phase is extracted with EtOAc and the combined organic phase is washed sequentially with H2O and saturated NaCl, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/8) to give the title compound as an off-white solid, 4.94 g (86%), mp 85-87° C., identified by NMR and mass spectral analyses.

후처리

  1. stirringstirred at room temperature overnight
  2. customThe resultant phases are separated
  3. extractionThe aqueous phase is extracted with EtOAc
  4. washthe combined organic phase is washed sequentially with H2O and saturated NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/8)

출처 및 근거

ORD 기록
ord-c2b820a941ae4219bcd93c5a3aa5d3d7
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919354B2

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