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

HRID 1671489Notes

Reaction equation

HRID 1671489 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 δ 1.31 (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-edf715677dc740edb26b638b4b98b017
Source dataset
uspto-grants-2011_08
Patent number
US07994312B2

Reaction notes

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