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

HRID 646217

Reaction equation

HRID 646217 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-1ff6724febe040d7a3ca943bfb82992f
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Linked notes

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