Sodium Hydroxide → 2-(5-methoxy-1H-indol-1-yl)acetic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]C)=[O:14])[CH:7]=[CH:6]2.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 2-(5-methoxy-1H-indol-1-yl)acetate (745 mg, 3.40 mmol) in MeOH (20 ml), aqueous 4N sodium hydroxide (935 μl, 3.74 mmol) was slowly added and the reaction was stirred at room temperature for 1 hour. The solvent was removed and the residue was partitioned between ethyl acetate and water. The aqueous phase was acidified with 2.5M HCl and extracted with ethyl acetate. This organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (510 mg, 2.485 mmol, 73% yield). MS/ESI+ 206.1 [MH]+.