Water → Methyl 3-[(1H-pyrrol-1-yl)methyl]benzoate

HRID 399840Notes

Reaction equation

HRID 399840 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14].O>CN(C)C=O>[N:1]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8027PyrroleHCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 18945150Methyl 3-[(1H-pyrrol-1-yl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of pyrrole (2.3 ml) and 60% sodium hydride (1.3 g) in N,N-dimethylformamide (50 ml) was added methyl 3-(bromomethyl)benzoate (5.0 g) under ice-cooling and the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract layer was washed with water, dried over magnesium sulfate and evaporated to give methyl 3-(pyrrol-1-yl)methylbenzoate (4.14 g) as an oil.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ac38464459e343f1941f9a30c73fca8e
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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