Water → 6-Fluoro-1H-indole-3-ethanol

HRID 2306979Notes

Reaction equation

HRID 2306979 reaction equation
C([O:3][C:4](=O)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[K+]>C1COCC1>[F:16][C:12]1[CH:11]=[C:10]2[C:15]([C:7]([CH2:5][CH2:4][OH:3])=[CH:8][NH:9]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 44596115HCID 44596115, compound

Product 1

HCID 122728176-Fluoro-1H-indole-3-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-fluoro-3-indoleglyoxylic acid ethyl ester (2.01 g, 8.55 mmol) in dry THF (0.11 L) at 0° C. under argon was added LiAlH4 (1.68 g, 44.2 mmol). The reaction mixture was refluxed for 3 h, cooled to 0° C., and treated with H2O (1.7 mL), 15% aq KOH (1.7 mL), and H2O (5 mL). The mixture was filtered. The filtrate was diluted with EtOAc, and washed with H2O and brine. The EtOAc solution was dried, filtered, and concentrated to give the title compound: TLC Rf=0.33 (9:1 CH2Cl2/Me2CO); MS (ESI−) m/z 178.0; 1H NMR (CDCl3, 300 MHz) δ 8.38 (1H), 7.49 (1H), 7.01-6.63 (3H), 3.90 (2H), 2.99 (2H), 2.23 (1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. filtrationThe mixture was filtered
  3. additionThe filtrate was diluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialThe EtOAc solution was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4d7bdbc7e4994ccb99d899a012b9ffa9
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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