Lithium Hydroxide → 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetic acid

HRID 571193Notes

Reaction equation

HRID 571193 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH2:12][C:13]([O:15]C)=[O:14])=[CH:5][CH:4]=1.[OH-].[Li+]>C1COCC1.O>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86681612methyl 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetate

Product 1

HCID 670827152-(6-(trifluoromethyl)-1H-indol-1-yl)acetic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetate (120 mg, 0.467 mmol) was dissolved in a mixture (1/1) of THF/H2O (4 ml), and lithium hydroxide (112 mg, 4.67 mmol) was added. The mixture was stirred at room temperature for 2 hours. The organic solvent was evaporated and 2N HCl was added to the resulting mixture (pH=5). The precipitate was collected by filtration affording 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetic acid (90 mg, 0.370 mmol, 79% yield). MS/ESI+ 244.0 [MH]+.

Workup

  1. additionwas added
  2. customThe organic solvent was evaporated
  3. addition2N HCl was added to the resulting mixture (pH=5)
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9de8cd8ed023461d85ef7c288be4ee07
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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