Potassium Carbonate → HCID 1244907, compound

HRID 1258952Notes

Reaction equation

HRID 1258952 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].Br[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[O:11]([CH2:10][CH2:9][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13854Pyrrole-2-carboxaldehydeHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 1244907HCID 1244907, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-pyrrole-2-carbaldehyde (0.45 g, 4.8 mmol) and 1-(2-bromoethoxy)benzene (1.1 g, 5.3 mmol) in DMF (20 mL) was added K2CO3 (3.3 g, 24 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 1.1 g (˜100%) of crude 1-(2-phenoxyethyl)-1H-pyrrole-2-carbaldehyde as a light yellow oil.

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-fffc6429316542c8b8df0b69d5337c5a
Source dataset
uspto-grants-2013_06
Patent number
US08466193B2

Reaction notes

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