Pyrrole → HCID 131717997, compound

HRID 1588375Notes

Reaction equation

HRID 1588375 reaction equation
[H-].[Na+].[C:3]1([B:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.O1CC[CH2:29][CH2:28]1>>[N:22]1([B-:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:26]=[CH:25][CH:24]=[CH:23]1.[CH2:23]([N+:22]([CH2:21][CH3:16])([CH2:28][CH3:29])[CH2:26][CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 8027PyrroleHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 70400Triphenylborane

Product 1

HCID 131717997HCID 131717997, compound

Procedure

A mixtue of sodium hydride (0.45 g, 19 mmole) and triphenylboron (3.6 g, 15 mmole) in tetrahydrofuran (100 ml) was slowly added to a stirred solution of pyrrole (1.01 g, 15 mmole) in anhydrous tetrahydrofuran. The mixture was stirred for five hours under nitrogen at room temperature, and the resulting dark solution was filtered through filter paper and diluted with an equal amount of water. An excess of tetraethylammonium chloride solution was added slowly and the precipitate which formed was collected, dissolved in acetone and purified by addition of the acetone solution to water. The product tetraethylammonium (1-pyrrole)triphenylborate was collected (4.52 g, 72%).

Workup

  1. filtrationthe resulting dark solution was filtered
  2. filtrationthrough filter paper
  3. additiondiluted with an equal amount of water
  4. additionAn excess of tetraethylammonium chloride solution was added slowly
  5. customthe precipitate which formed
  6. customwas collected
  7. dissolutiondissolved in acetone
  8. custompurified by addition of the acetone solution to water
  9. customThe product tetraethylammonium (1-pyrrole)triphenylborate was collected (4.52 g, 72%)

Sources & evidence

ORD record
ord-cae19e5d231f46d5a1f0e442c4e1fe5f
Source dataset
uspto-grants-1993_06
Patent number
US05221761

Reaction notes

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