Indole-3-Acetic Acid → Tryptophol

HRID 1506937Notes

Reaction equation

HRID 1506937 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11](O)=[O:12])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1

Participants

4

Reactant 2

HCID 802Indole-3-Acetic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10685TryptopholYield 27%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Indole-3-acetic acid (5 g, 28.54 mmol) was dissolved in diethyl ether (100 mL) and the solution was cooled to 0° C. Lithium aluminum hydride (1.19 g, 31.39 mmol) was added thereto, followed by stirring for 4 hours. The reaction was terminated with the addition of water and a 10% sodium hydroxide solution. The reaction mixture was filtered through celite and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound (1.24 g, 27%).

Workup

  1. customThe reaction was terminated with the addition of water
  2. filtrationThe reaction mixture was filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-4a5c363197554884bc745d1fc901a781
Source dataset
uspto-grants-2015_12
Patent number
US09221790B2

Reaction notes

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