Water → 6-Fluoro-1H-indole-3-ethanol

HRID 1370415Notes

Reaction equation

HRID 1370415 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-872d82e06bdf405f817fd100ece9bb29
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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