Water → HCID 8543774, compound

HRID 2384083Notes

Reaction equation

HRID 2384083 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[CH2:16]([O:7][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12473Pyrrole-2-Carboxylic Acid

Product 1

HCID 8543774HCID 8543774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1H-pyrrole-2-carboxylic acid (1.11 g, 10 mmol) in DMF (15 mL) is added potassium carbonate (2.07 g, 15 mmol) and (bromomethyl)benzene (1.80 g, 10.50 mmol). After stirring the mixture at room temperature for 18 hours, water is added and the mixture is extracted three times with ethyl acetate. The combined organic layers are washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (heptane/ethyl acetate=5:1) to give 1H-pyrrole-2-carboxylic acid benzylester.

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialthen is dried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by flash chromatography (heptane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-eac788a842e448be8efa44eedabbfaf4
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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