Tetrabutylammonium Fluoride → 2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamine

HRID 1265291Notes

Reaction equation

HRID 1265291 reaction equation
C[Si](C)(C)CCOC(=O)[NH:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]2[N:8]([NH2:7])[C:9]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][CH:28]=3)=[CH:10][CH:11]=2)=[CH:18][CH:17]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59050403[2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester

Product 1

HCID 186154682,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester (681 mg, 1.39 mmol) was treated with a 1 M solution of TBAF in THF (2.78 mL). The resulting solution was stirred at rt overnight, then quenched with glacial acetic acid (0.155 mL). The solution was passed through a short plug of silica gel, eluting with toluene and concentrated in vacuo to afford 2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamine (299 mg, 80% for two steps) as a creamy white solid: 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 1.36 (s, 18H), 4.60 (s, 2H), 6.24 (s, 2H), 7.46 (d, 4H, J=8.7 Hz), 7.52 (d, 4H, J=8.7 Hz).

Workup

  1. customquenched with glacial acetic acid (0.155 mL)
  2. washeluting with toluene
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9b6462e8c744aebbefc5792e57f6a31
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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