5-Hydroxyindoleacetic Acid → Tryptophol

HRID 1951763Notes

Reaction equation

HRID 1951763 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.O[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH2:22][C:23](O)=[O:24]>O>[OH:24][CH2:23][CH2:22][C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[CH:13][CH:14]=2)[NH:18][CH:17]=1

Participants

5

Reactant 3

HCID 18265-Hydroxyindoleacetic AcidHCID 8028Tetrahydrofuran3×HCID 21226445Aluminium lithium hydride

Product 1

HCID 10685Tryptophol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

LiAlH4 (1.99 g, 52.3 mmol) was placed in abs. THF (60 ml), under argon, and (5-hydroxy-1H-indol-3-yl)-acetic acid (5.00 g, 26.2 mmol) in abs. THF (100 ml) was added in the course of 30 min. The mixture was boiled for 3 h under reflux. For working up, THF (10 ml) and H2O (4 ml) were added to the mixture, while cooling with ice, and stirring was carried out for 30 min. The mixture was filtered over Celite and rinsed with dichloromethane (150 ml), and the filtrate was concentrated in vacuo.

Workup

  1. temperatureunder reflux
  2. temperaturewhile cooling with ice
  3. waitwas carried out for 30 min
  4. filtrationThe mixture was filtered over Celite
  5. washrinsed with dichloromethane (150 ml)
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ac68f2565b364b4ab0f6175fc7e90330
Source dataset
uspto-grants-2013_03
Patent number
US08404740B2

Reaction notes

Loading…