Water → Indole-3-propanol

HRID 47255

Reaction equation

HRID 47255 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.[OH-].[Na+]>O1CCCC1>[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 962Water2×HCID 37441H-Indole-3-propanoic acidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 77115Indole-3-propanolYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of litium aluminum hydride (8.0 g) in tetrahydrofuran (500 mL) was a solution of 3-indolepropionic acid (20 g) in tetrahydrofuran (100 mL) added dropwise. The reaction mixture was stirred for 1 h at room temperature and subsequently cooled to 5° C. After sequential addition of water (16 mL), 15% aqueous sodium hydroxide (8.0 mL) and water (40 mL), the reaction mixture was stirred at room temperature over night and filtered. Evaporation of the volatile solvents gave pure 3-(1H-indol-3-yl)propanol (19.1 g) as an oil. 3-(1H-Indol-3-yl)propanol (18.6 g) and carbon tetrabromide (42.1 g) was dissolved in acetonitrile (1 L) and cooled to 0° C. and triphenylphosphine (30.7 g) was added in small portions. The reaction was stirred for further 3 h at room temperature, the volatile solvents evaporated in vacuo and the remaining oil purified by silicagel chromatography (heptane:ethyl acetate/2:1) to give 3-(3-bromopropyl)-1H-indole (25.6 g).

Workup

  1. additionadded dropwise
  2. temperaturesubsequently cooled to 5° C
  3. stirringthe reaction mixture was stirred at room temperature over night
  4. filtrationfiltered
  5. customEvaporation of the volatile solvents

Sources & evidence

ORD record
ord-b46c32a47f7e488b89de937541f39ed3
Source dataset
uspto-grants-2004_03
Patent number
US06699864B2

Linked notes

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