Water → Methyl 2-(2-benzoylpyrrol-1-yl)acetate

HRID 1742013Notes

Reaction equation

HRID 1742013 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].O>CN(C=O)C>[C:7]([C:15]1[N:16]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:17]=[CH:18][CH:19]=1)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24370Phenyl(1H-pyrrol-2-YL)methanoneHCID 60984Methyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 6618880Methyl 2-(2-benzoylpyrrol-1-yl)acetateYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Potassium tert-butoxide (7.22, 0.064 mol) was dissolved in DMF (40 ml) and 2-benzoylpyrrole (10 g, 0.058 mol) in DMF (10 ml) was added dropwise with stirring at room temperature. This was left for 16 hours then cooled to 0° C. when methyl bromoacetate (5.4 ml, 0.058 mol) in DMF (5 ml) was added dropwise. The reaction mixture was stirred for 16 hours then poured into water (150 ml) and extracted with diethyl ether (2×100 ml). The extracts were washed with brine (2×75 ml) dried and evaporated to give methyl (2-benzoylpyrrol-1-yl)acetate (12.6 g, 89%) as a brown oil which crystallised on standing.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 16 hours
  3. extractionextracted with diethyl ether (2×100 ml)
  4. washThe extracts were washed with brine (2×75 ml)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-81aee9547bc44849bcda04b1d38e64df
Source dataset
uspto-grants-1994_08
Patent number
US05336682

Reaction notes

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