Acetic Acid → 1-(4-Methylphenyl)-1H-pyrrole

HRID 2379737Notes

Reaction equation

HRID 2379737 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.CO[CH:11]1[CH2:15][CH2:14][CH:13](OC)O1.C(O)(=O)C>CCCCCC>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:11]=[CH:15][CH:14]=[CH:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7813p-ToluidineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2724261-(4-Methylphenyl)-1H-pyrroleYield 45%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-100 °C

Procedure

The title compound was prepared in analogy to the procedure described in European Patent Application 480204. 4-Methylaniline (30 g, 280 mmol), 2,5-dimethoxytetrahydrofuran (22 g, 166 mmol) and acetic acid (200 mL) were combined under a nitrogen atmosphere and heated at -100° C. for 90 minutes. The solvent was removed under reduced pressure and the residue obtained suspended in hexane and filtered. The filtrate was passed through a pad of silica gel and concentrated in vacuo. The residue obtained was crystallized from methanol to afford 10.6 g (45%) of the title compound. MS (DCI/NH3) m/e 158 (M+H)+.

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. customThe solvent was removed under reduced pressure
  3. customthe residue obtained
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas crystallized from methanol

Sources & evidence

ORD record
ord-b8e3942eb9ff4abe87126f4ae5701b49
Source dataset
uspto-grants-1994_11
Patent number
US05364869

Reaction notes

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