Sodium Hydroxide → HCID 20529122, compound

HRID 66906Notes

Reaction equation

HRID 66906 reaction equation
Cl.[CH3:2][C:3]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH3:20])[C:13]([CH3:21])=[C:12]2[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:7])[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH3:2][C:3]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH3:20])[C:13]([CH3:21])=[C:12]2[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:7])[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3059433Propanoic acid, 2-methyl-2-((2-methyl-1-propyl-3-(4-pyridinyl)-1H-indol-5-yl)oxy)-, hydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 20529122HCID 20529122, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.0 g (2.6 m mole) of 2-methyl-2-[2-methyl-1-propyl-3-(4-pyridyl)-1H-indole-5-yloxy]propanoic acid hydrochloride was added dropwise to 1.0 g (26 m mole) of lithiumaluminium hydride in 50 ml of absolute tetrahydrofurane under stirring. After the mixture was stirred for one hour at 60° C., 2 N sodium hydroxide solution was added. The sodium aluminate precipitate was filtered off, and the residue was evaporated and purified on silicagel by colunn chromatography (eluant: ethyl acetate).

Workup

  1. stirringAfter the mixture was stirred for one hour at 60° C.
  2. filtrationThe sodium aluminate precipitate was filtered off
  3. customthe residue was evaporated
  4. custompurified on silicagel by colunn chromatography (eluant: ethyl acetate)

Sources & evidence

ORD record
ord-80dde7d61fd2441fa791caf5c2e34505
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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