Hydrochloric Acid → 1H-Pyrrol-1-ylacetic acid

HRID 1611417Notes

Reaction equation

HRID 1611417 reaction equation
[OH-].[K+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.Br[CH2:9][C:10]([O:12]CC)=[O:11].Cl>O.CS(C)=O>[N:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4]1

Participants

7

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% HCl (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-82b5fe7fe4db441783fc2959a1d8b150
Source dataset
uspto-grants-2006_01
Patent number
US06987123B2

Reaction notes

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