Sodium Hydroxide → 1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylic acid

HRID 1590576Notes

Reaction equation

HRID 1590576 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[C:4]([C:11]([O:13]CC)=[O:12])=[CH:3]1.[OH-].[Na+]>C(O)C.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([F:9])([F:10])[F:8])[C:4]([C:11]([OH:13])=[O:12])=[CH:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21459511ethyl 1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 117887791-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 1-methyl-4-(trifluoromethyl)pyrrole-3-carboxylate (4.4 g, 0.02 mol) and 4N sodium hydroxide (5 ml, 0.02 mol) in ethanol is stirred for 24 hours at room temperature, diluted with water and extracted with ether. The aqueous phase is acidified with 10% HCl and filtered. The filter cake is washed with water and dried in vacuo at 45° C. to afford the title compound as an off-white solid, 2.4 g (62%), mp 210°-212° C.

Workup

  1. extractionextracted with ether
  2. filtrationfiltered
  3. washThe filter cake is washed with water
  4. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-fbf6ec8996884061aa6a11a9dc8e3317
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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