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

HRID 748073Notes

Reaction equation

HRID 748073 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[CH:6]=[O:7])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chloride

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 KO'Bu (1.2 g, 10.5 mmol), Et4N+T (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-bd2fedcfd9b04d1993ad1aa2aba77e45
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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