Tetrahydrofuran → 1-ethyl-1H-indole-3-carboxylic acid

HRID 489614Notes

Reaction equation

HRID 489614 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][CH3:15])[CH:6]=1)=[O:4].C1COCC1.[OH-].[Na+]>CO>[CH2:14]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:3]([OH:4])=[O:2])=[CH:6]1)[CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5191495Methyl 1-ethylindole-3-carboxylate

Product 1

HCID 36971601-ethyl-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-ethyl-1H-indole-3-carboxylic acid methyl ester (1.8 g, 8.8 mmol) was stirred in a 1:1 mixture of THF:MeOH (40 mL), and to this was added 2N NaOH (20 mL). The reaction was heated at reflux for 4 hours. The reaction mixture was partially evaporated to remove the THF, MeOH and the remaining material diluted with water (20 mL) and acidified to pH=2 with 1N HCl. The mixture was extracted with dichloromethane (100 mL), dried over sodium sulfate and evaporated under reduced pressure to give the title compound as a white solid, which was used directly in the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 hours
  3. customThe reaction mixture was partially evaporated
  4. customto remove the THF, MeOH
  5. additionthe remaining material diluted with water (20 mL)
  6. extractionThe mixture was extracted with dichloromethane (100 mL)
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1a1adcdf9bd94901ac30f1041428d926
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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