Pyrrole → 2,2'-[(4-tert-Butylphenyl)methylene]di(1H-pyrrole)

HRID 1931531Notes

Reaction equation

HRID 1931531 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[OH-].[Na+]>>[CH3:2][C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]([C:14]2[NH:13][CH:17]=[CH:16][CH:15]=2)[C:17]2[NH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 8027PyrroleHCID 14798Sodium HydroxideHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 42453552,2'-[(4-tert-Butylphenyl)methylene]di(1H-pyrrole)Yield 79%

Procedure

Following a general procedure,8 a solution of 4-tert-butylbenzaldehyde (16.2 g, 100 mmol) in pyrrole (694 mL, 10.0 mol) at room temperature under argon was treated with InCl3 (2.21 g, 10.0 mmol) for 1.5 h. Powdered NaOH (12.0 g, 300 mmol) was added. After stirring for 1 h, the mixture was suction filtered and excess pyrrole was removed under high vacuum. The residue was treated with hexanes (3×100 mL) to facilitate removal of traces of pyrrole. The resulting solid was recrystallized [EtOH/H2O (6:1)], affording a grayish white solid (21.6 g, 79%): mp 155-157° C.; 1H NMR δ1.31 (s, 9H), 5.45 (s, 1H), 5.94-5.96 (m, 2H), 6.15-6.17 (m, 2H), 6.68-6.70 (m, 2H), 7.13-7.16 (m, 2H), 7.32-7.35 (m, 2H), 7.89-7.95 (br, 2H); 13C NMR δ 31.5, 34.6, 43.6, 107.2, 108.5, 117.2, 125.7, 128.2, 132.9, 139.1, 149.9; FAB-MS obsd 278.1788, calcd 278.1783 (C19H22N2). Anal. Calcd for C19H22N2: C, 81.97; H, 7.97; N, 10.06. Found: C, 81.82; H, 7.96; N, 10.05. The data (1H NMR, mp, elemental analysis) are consistent with those obtained from samples prepared via earlier routes.2

Workup

  1. customat room temperature
  2. filtrationfiltered
  3. customexcess pyrrole was removed under high vacuum
  4. additionThe residue was treated with hexanes (3×100 mL)
  5. customremoval of traces of pyrrole
  6. customThe resulting solid was recrystallized [EtOH/H2O (6:1)]

Sources & evidence

ORD record
ord-ac9d0fa9a5f3425ab8e8accc8678531d
Source dataset
uspto-grants-2012_05
Patent number
US08188298B2

Reaction notes

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