Sodium Hydroxide → 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid

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Reaction Steps

General Procedure 2 A solution of ethyl 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylate (Compound 1, 873 mg, 2.83 mmol) and NaOH (2.2 g, 56 mmol) in EtOH (10 ml) and H2O (10 ml) was heated to 90° C. for 16 h. The reaction was quenched with 6M HCl (10 ml), extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes to 20% MeOH-EtOAc) to yield 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid (Compound 2) as a reddish brown solid.

Provenance & Evidence