Water → Indole-3-propanol

HRID 1168848Notes

Reaction equation

HRID 1168848 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[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.O.OS(O)(=O)=O>C(OCC)C>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 37441H-Indole-3-propanoic acidHCID 21226445Aluminium lithium hydrideHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 77115Indole-3-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of lithium aluminum hydride (4.68 g, 126 mmol) in 230 mL anhydrous diethylether was stirred heavily. 3-Indole propionic acid (10.0 g, 53 mmol) dissolved in 460 mL anhydrous diethylether was transferred to a dropping funnel and added at such a rate that gentle reflux was maintained. The reaction mixture was left with stirring at reflux temperature for 2 h, then at room temperature overnight. Then reflux was continued for 2 h before cooling to room temperature. 25 mL H2O was slowly added followed by 70 mL H2O/H2SO4 (1:3H2O/H2SO4). The resulting clear mixture was extracted with 110 mL diethylether three times. The combined organic phases were washed with brine, dried with Na2SO4, filtrated and concentrated to bright oil, which was used without further purification.

Workup

  1. customwas transferred to a dropping funnel
  2. additionadded at such a rate
  3. temperaturethat gentle reflux
  4. temperaturewas maintained
  5. waitThe reaction mixture was left
  6. stirringwith stirring
  7. temperatureat reflux temperature for 2 h
  8. customat room temperature
  9. customovernight
  10. temperatureThen reflux
  11. extractionThe resulting clear mixture was extracted with 110 mL diethylether three times
  12. washThe combined organic phases were washed with brine
  13. dry with materialdried with Na2SO4
  14. filtrationfiltrated
  15. concentrationconcentrated to bright oil, which
  16. customwas used without further purification

Sources & evidence

ORD record
ord-5c22e255943b4294b508bfaf44398b7b
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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