5-Fluoroindole-3-acetic acid → 2-(5-fluoro-1H-indol-3-yl)ethanol

HRID 1954223Notes

Reaction equation

HRID 1954223 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12](O)=[O:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 967505-Fluoroindole-3-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 136162482-(5-fluoro-1H-indol-3-yl)ethanolYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-fluoro-indol-3-acetic acid (4.3 g, 0.022 mol) in anhydrous THF (35 ml) was added LiAlH4 (1.0 M, 33 ml, 0.033 mol) at 0° C. The mixture was allowed to stir for 0.5 hours and, then quenched by saturated NH4Cl solution. The mixture was then filtered through celite. The filtrate was washed with 1N NaOH (3×100 ml) and extracted with ethyl acetate (3×100 ml). The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was removed under vacuum. Chromatography (10% methanol-methylene chloride) afforded 4.04 g (100%) of product as an off-white solid: mp 59-61° C.

Workup

  1. customquenched by saturated NH4Cl solution
  2. filtrationThe mixture was then filtered through celite
  3. washThe filtrate was washed with 1N NaOH (3×100 ml)
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c0e4a4c8a46d4d608a17434ba18dcc7e
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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