Indole-3-Acetic Acid → Tryptophol

HRID 1461702Notes

Reaction equation

HRID 1461702 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17](O)=[O:18])=[CH:8]1.O.[OH-].[Na+]>C1COCC1>[OH:18][CH2:17][CH2:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][CH:8]=1

Participants

6

Reactant 4

HCID 802Indole-3-Acetic AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 10685TryptopholYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LiAlH4 (3.24 g) in THF (200 mL) at 0° C. and under N2 atmosphere was added dropwise a THF solution (50 mL) containing indole-3-acetic acid (10.0 g). After the addition was complete, the reaction was heated at reflux for 3 h, after which time the mixture was cooled to 0° C. and water (3.3 mL) added, followed by 15% NaOH (3.3 mL), and finally additional water (9.9 mL). The reaction was filtered and the filter cake washed with Et2O. The organic layers were combined, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure to yield 3-(2-hydroxyethyl)indole (VI; 7.4 g; 80%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 3 h
  4. filtrationThe reaction was filtered
  5. washthe filter cake washed with Et2O
  6. dry with materialdried with anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44a4d90fa567439f8ce710338777afd8
Source dataset
uspto-grants-1991_12
Patent number
US05077293

Reaction notes

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