Potassium Carbonate → 1-(4-Methoxy-benzyl)-1H-pyrrole-2-carbaldehyde

HRID 1400666Notes

Reaction equation

HRID 1400666 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].Cl[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[CH:6]=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13854Pyrrole-2-carboxaldehydeHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 64931691-(4-Methoxy-benzyl)-1H-pyrrole-2-carbaldehydeYield 110.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-pyrrole-2-carbaldehyde (0.58 g, 6.1 mmol) and 1-(chloromethyl)-4-methoxybenzene (1.0 mL, 7.3 mmol) in DMF (15 mL) was added K2CO3 (3.4 g, 24.5 mmol). After stirring 16 hr at room temperature, the mixture was diluted with ethyl acetate (200 mL) and washed with H2O (2×100 mL) then brine (100 mL). The organic layer was dried (MgSO4), filtered and then concentrated to provide 1.45 g (˜100%) of crude 1-(4-methoxybenzyl)-1H-pyrrole-2-carbaldehyde. This material was used without further purification.

Workup

  1. washwashed with H2O (2×100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-788b5421380f46fdabad0f63b3c9fc69
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

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