Dimethyl Sulfoxide → 1H-Pyrrol-1-ylacetic acid

HRID 2252966Notes

Reaction equation

HRID 2252966 reaction equation
[OH-].[K+].CS(C)=O.[NH:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.Br[CH2:13][C:14]([O:16]CC)=[O:15]>O>[N:7]1([CH2:13][C:14]([OH:16])=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7748Ethyl bromoacetateHCID 8027PyrroleHCID 14797Potassium Hydroxide

Product 1

HCID 2420271H-Pyrrol-1-ylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of potassium hydroxide (16.7 g) and dry DMSO (150 mL), pyrrole (5 g) was added dropwise at 20-25° C., with stirring under nitrogen atmosphere. Stirring was continued for 1 hr at 20-25° C. Ethyl bromoacetate (24.5 g) was added dropwise at 20-25° C. and stirring was continued for 2 hr. In the reaction mixture (150 mL) DM water was added and pH was made acidic (pH=3) with 20% HCI (50 mL). The reaction mixture was extracted with diethyl ether (2×100 mL). The combined organic extract was washed with DM water (100 mL), saturated brine (100 mL) and dried over Na2SO4. The solvent was evaporated to obtain pyrrol-1-yl-acetic acid.

Workup

  1. additionwas added dropwise at 20-25° C.
  2. stirringStirring
  3. stirringstirring
  4. waitwas continued for 2 hr
  5. extractionThe reaction mixture was extracted with diethyl ether (2×100 mL)
  6. extractionThe combined organic extract
  7. washwas washed with DM water (100 mL), saturated brine (100 mL)
  8. dry with materialdried over Na2SO4
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2a1eb190d0104ef19d35982f9a85b105
Source dataset
uspto-grants-2008_01
Patent number
US07323491B2

Reaction notes

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