Sodium Hydroxide → 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol

HRID 447747Notes

Reaction equation

HRID 447747 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([CH2:11][C:12](OCC)=[O:13])[C:5]=2[CH:4]=[CH:3]1.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([CH2:11][CH2:12][OH:13])[C:5]=2[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20761741ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetate

Product 1

HCID 578144052-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetate (0.22 g, 1.00 mmol) in THF anh. is added slowly over a suspension of AlLiH4 (0.1 g, 2.63 mmol) in THF anh. (10 mL) cooled in an ice bath. The mixture is maintained under stirring at room temperature for 1 hour and then is refluxed for 3 hours. The mixture is hydrolyzed with ice and NaOH (10%), filtered and the solvent is evaporated under reduced pressure. The residue is dissolved in ethyl acetate and washed with water. The organic phase is removed at reduced pressure and the resulting crude is purified by column chromatography, giving 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol (0.15 g, 0.84 mmol, 84%, oil). 1H NMR (300 MHz, CDCl3): δ 1.37 (m, 1H), 1.68 (m, 3H), 1.92 (m, 3H), 2.49 (m, 2H), 2.78 (m, 1H), 3.46 (s, 3H), 3.81 (m, 2H), 5.99 (d, J=2.5 Hz, 1H), 6.50 (d, J=2.5 Hz, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture is maintained
  3. temperatureis refluxed for 3 hours
  4. filtrationfiltered
  5. customthe solvent is evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed with water
  8. customThe organic phase is removed at reduced pressure
  9. customthe resulting crude is purified by column chromatography

Sources & evidence

ORD record
ord-f59fcd899c364e788a61ae3c05ede5c1
Source dataset
uspto-grants-2013_07
Patent number
US08481567B2

Reaction notes

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