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

HRID 2220439Notes

Reaction equation

HRID 2220439 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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)−.

Workup

  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)

Sources & evidence

ORD record
ord-81eb66d0faf046609e9bbb330e8d1602
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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