Sodium Hydroxide → (5-chloro-1H-indol-2-yl)methanol

HRID 2301667Notes

Reaction equation

HRID 2301667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](OCC)=[O:12])=[CH:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 21226445Aluminium lithium hydride4×

Product 1

HCID 12203316(5-chloro-1H-indol-2-yl)methanolYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-chloro-2-indole-carboxylate (1 eq) was dissolved in THF (0.45M) under N2. This solution was cooled to 0° C. for fifteen minutes and then 1.1 eq LiAlH4 (1M in THF) was added. The resulting dark brown solution was allowed to return to rt with stirring and kept overnight. Then water (1/25 of the volume of the LiAlH4 solution) was added slowly, followed by 15% NaOH(aq) (1/25 of the volume of the LiAlH4 solution) solution. Finally, water (1/25 of the volume of the LiAlH4 solution) was added along with a large amount of MgSO4. Solution was filtered and the solid was washed with EtOAc and the filtrate was collected. Solvent was stripped off to give (5-chloro-1H-indol-2-yl)methanol (yellow solid) in 85% yield.

Workup

  1. customto return to rt
  2. filtrationSolution was filtered
  3. washthe solid was washed with EtOAc
  4. customthe filtrate was collected

Sources & evidence

ORD record
ord-628d322a666f46598470aa191acd5e9e
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

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