Water → Indole-3-propanol

HRID 1031489Notes

Reaction equation

HRID 1031489 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][CH2:17][C:18](O)=[O:19])=[CH:8]1.O.[OH-].[Na+]>C1COCC1>[OH:19][CH2:18][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 962Water2×HCID 37441H-Indole-3-propanoic acidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 77115Indole-3-propanolYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LiAlH4 (4.02 g) in THF (200 mL) at 0° C. and under N atmosphere was added dropwise a THF solution (100 mL) containing indole-3-propanoic acid (20.0 g). After the addition was complete, the reaction was heated at reflux for 16 h, after which time the mixture was cooled to 0° C. and water (4 mL) added, followed by 15% NaOH (4 mL), and finally additional water (12 mL). The reaction was filtered and the THF filtrate extracted with 5% NaOH (4 mL), and finally additional water (12 mL). The reaction was filtered and the THF filtrate extracted with 5% NaHCO3 followed by a sat. NaCl solution. The organic phase was dried with anhydrous K2CO3, filtered, and concentrated under reduced pressure to yield 3-(3-hydroxypropyl)indole (VI; 7.5 g; 41%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 16 h
  4. filtrationThe reaction was filtered
  5. extractionthe THF filtrate extracted with 5% NaOH (4 mL), and finally additional water (12 mL)
  6. filtrationThe reaction was filtered
  7. extractionthe THF filtrate extracted with 5% NaHCO3
  8. dry with materialThe organic phase was dried with anhydrous K2CO3
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b26dbeaa72f64c4ead18447007292e93
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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