Pyrrole-2-carboxaldehyde → 1-(4-Methoxy-benzyl)-1H-pyrrole-2-carbaldehyde

HRID 2243149Notes

Reaction equation

HRID 2243149 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].CC([O-])(C)C.[K+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1.[Cl-].[NH4+]>C1COCC1>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[CH:6]=[O:7])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 13854Pyrrole-2-carboxaldehydeHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 64931691-(4-Methoxy-benzyl)-1H-pyrrole-2-carbaldehydeYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To pyrrole-2-carboxaldehyde (1.0 g, 10.5 mmol) in THF (60 mL) was added KOtBu (1.2 g, 10.5 mmol), Et4N+I− (100 mg) and 4-methoxybenzyl chloride (1.4 mL, 10.5 mmol). After 1 day saturated aqueous ammonium chloride was added and the mixture was extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated. Column chromatography (EtOAc/hexanes, 1:9) provided 1.48 g (65%) of 1-(4-methoxybenzyl)-1H-pyrrole-2-carbaldehyde as an oil.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25504754ccdd4dac9f527c1eca62ad67
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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