Sodium Hydroxide → (1H-indol-5-yl)methanol

HRID 2120235Notes

Reaction equation

HRID 2120235 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-].[OH-].[Na+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

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

Product 1

HCID 2773458(1H-indol-5-yl)methanolYield 108.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Indole-5-carboxylic acid (5.02 g, 31.3 mmol) in tetrahydrofuran (40 mL) was added slowly to the lithium aluminium hydride (1.88 g, 49.5 mmol) stirred in tetrahydrofuran (125 mL) under nitrogen with external heating so as to maintain a gently reflux. The mixture was heated at reflux for 2 hours and cooled to room temperature. 2 N sodium hydroxide (10 mL) was then added dropwise to the reaction mixture. The precipitate was removed by filtration and the filtrate was concentrated. It was dissolved in dichloromethane (80 mL), washed with 2 N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate and concentrated to give about 5 g of (1H-indol-5-yl)-methanol.

Workup

  1. temperaturewith external heating so as
  2. temperatureto maintain
  3. temperaturea gently reflux
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 2 hours
  6. customThe precipitate was removed by filtration
  7. concentrationthe filtrate was concentrated
  8. dissolutionIt was dissolved in dichloromethane (80 mL)
  9. washwashed with 2 N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6e5644d7a3254128a91adeffed2f76b9
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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