Ethanol → HCID 18455625, compound

Participants

Reaction Steps

Ethyl 5-(2-methoxyethoxy)-1H-indole-2-carboxylate (2.0 g, 7.4 mmol) in THF (20 ml) was treated with a solution of LiOH•H2O (0.62 g, 14.8 mmol) in water (10 ml). Ethanol was added until a homogenous solution formed and stirring was continued for 16 h. The reaction mixture was diluted with water (50 ml) and the organic solvents were removed in vacuo. The pH was adjusted to 4 with 1M aqueous HCl and the aqueous solution was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 5-(2-methoxyethoxy)-1H-indole-2-carboxylic acid (1.7 g, 7.2 mmol) as a white solid. The crude acid was directly used without further purification.

Provenance & Evidence