Indole-3-Acetic Acid → Indole-3-propanol

HRID 1031490Notes

Reaction equation

HRID 1031490 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)=[CH:8]1.O.[OH-].[Na+].C1C[O:26][CH2:25]C1>>[OH:26][CH2:25][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 5

HCID 802Indole-3-Acetic AcidHCID 962Water2×HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 77115Indole-3-propanolYield 80%

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LiAlH4 (3.24g) in THF (200 mL) at 0° C. and under N2 atmosphere was added tropwise 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-(2hydroxyethyl)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-84e9385837e842b682f10d75692ccbdd
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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