Water → 1-(3-bromophenyl)-2-(1H-pyrrol-3-yl)ethane-1,2-dione

HRID 2220439

반응식

HRID 2220439 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:14]=[CH:13][N:12]([Si](C(C)C)(C(C)C)C(C)C)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[O-:25]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+].[O-][Mn](=O)(=O)=O.[K+].[OH2:42]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:25])[C:9]([C:10]2[CH:14]=[CH:13][NH:12][CH:11]=2)=[O:42])[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 687008993-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole

생성물 1

HCID 597726681-(3-bromophenyl)-2-(1H-pyrrol-3-yl)ethane-1,2-dione수율 42%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole (2.7 g, 8.5 mmol) in acetone (100 mml) is added a solution of MgSO4 (1.53 g, 12.75 mmol) and NaHCO3 (316 mg, 3.76 mmol) in water (50 ml), followed by the addition of KMnO4 (2.68 g, 17 mmol) in one portion at room temperature. After refluxing for 5 h, the reaction mixture is cooled to room temperature and extracted with ether (2×50 mL), the combined organic extracts are dried over MgSO4. The crude material is purified flash chromatography (silica gel, EtOAc/hexane: 30/70 to 50/50) to afford the title compound as a yellow solid (42%). mp: 111-113° C. MS (−) ES: 276 (M−H)−.

후처리

  1. temperatureAfter refluxing for 5 h
  2. extractionextracted with ether (2×50 mL)
  3. dry with materialthe combined organic extracts are dried over MgSO4
  4. customThe crude material is purified flash chromatography (silica gel, EtOAc/hexane: 30/70 to 50/50)

출처 및 근거

ORD 기록
ord-81eb66d0faf046609e9bbb330e8d1602
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417047B2

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