Aluminium lithium hydride → 2-(5-fluoro-1H-indol-3-yl)ethanol

HRID 1461703Notes

Reaction equation

HRID 1461703 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=2)[NH:15][CH:14]=1)=O)C>C1COCC1>[F:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:11][CH2:10][OH:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53961461Ethyl 2-(5-Fluoro-3-indolyl)-2-oxoacetate

Product 1

HCID 136162482-(5-fluoro-1H-indol-3-yl)ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (8.60 g, 0.23 mole) in 400 mL of dry THF was added 5-fluoro-3-indoleglyoxylic acid ethyl ester (13.50 g, 0.057 mole) portionwise at room temperature. Preparation of this ester intermediate is given hereinbelow. The mixture was heated to reflux under Ar for 1 h and was then cooled at 0° C. and quenched according to the method of Fieser (Fieser and Fieser, "Reagents for Organic Synthesis", Vol. 1, pg. 584). The resulting slurry was filtered and the filter cake was washed with THF. The filtrate was dried (Na2SO4) and evaporated to give the product (10.00 g, 100%) as a yellow oil. It was used as such without further purification; IR (neat) 3420 cm-1. 1Hnmr (80 MHz, CDCl3). δ: 7.73 (br s, 1H), 7.1-6.4 (m, 4H), 3.57 (t, J=8 Hz, 2H), 2.66 (t, J=8 Hz, 2H), 1.20 (br s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under Ar for 1 h
  3. customquenched
  4. customaccording to the method of Fieser (Fieser and Fieser, "Reagents for Organic Synthesis", Vol. 1, pg. 584)
  5. filtrationThe resulting slurry was filtered
  6. washthe filter cake was washed with THF
  7. dry with materialThe filtrate was dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-b6116cea7b4b4d8298bd8ce4fe33fa21
Source dataset
uspto-grants-1991_12
Patent number
US05077293

Reaction notes

Loading…