Sodium Hydroxide → 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).