Ethyl Acetate → Indole-5-carboxaldehyde

HRID 618086Notes

Reaction equation

HRID 618086 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](O)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 742801H-Indole-5-Carboxylic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 589040Indole-5-carboxaldehydeYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Indole-5-carboxylic acid (3.10 g) was dissolved in tetrahydrofuran (50 ml), and lithium aluminium hydride (1.50 g) was added thereto, followed by heating under reflux for 20 hours. The reaction solution was cooled to room temperature, and ethyl acetate and then a 2N aqueous solution of sodium hydroxide were added thereto to cease the reaction. The reaction solution was dried over anhydrous sodium sulfate and insoluble matters were filtered off. Manganese dioxide (30.00 g) was added to the filtrate, followed by stirring at room temperature for 96 hours. Insoluble matters were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give indole-5-carbaldehyde (1.43 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 20 hours
  3. customthe reaction
  4. dry with materialThe reaction solution was dried over anhydrous sodium sulfate and insoluble matters
  5. filtrationwere filtered off
  6. additionManganese dioxide (30.00 g) was added to the filtrate
  7. filtrationInsoluble matters were filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4a1c24f2585b4614bd502eb1658a2b2f
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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