Tetrahydrofuran → 5-(1,1-Dimethylethyl)-1H-indole-2-carboxylic acid

HRID 1604625Notes

Reaction equation

HRID 1604625 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16]CC)=[O:15])=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([OH:16])=[O:15])=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 4714960ethyl 5-tert-butyl-1H-indole-2-carboxylate

Product 1

HCID 46422295-(1,1-Dimethylethyl)-1H-indole-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 5-tert-butylindole-2-carboxylate (3.0 g) and 1N sodium hydroxide solution into a mixed solvent of tetrahydrofuran (20 ml) and methanol (10 ml) was stirred at 40° C. for 5 hours. After removal of solvent, the resulting aqueous solution was made acidic with diluted hydrochloric acid. The resulting precipitates were collected by filtration and washed with water to give 5-tert-butylindole-2-carboxylic acid (2.47 g).

Workup

  1. customAfter removal of solvent
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-a368667c31004cfebab55819c953ed57
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…