Methanol → HCID 68480834, compound

Participants

Reaction Conditions

Reaction Steps

A methanol solution of ethyl 5-{[2-(methylthio)ethyl]oxy}-1H-indole-2-carboxylate (0.099 g, 0.356 mmol) was treated with 1 N LiOH (4 mL). The reaction mixture turned cloudy and THF was added until the cloudiness disappeared. The reaction was heated to 70° C. until TLC showed consumption of the starting material. The reaction mixture was partitioned between EtOAc and water and the basic layer was separated. The basic layer was acidified with conc. HCl and extracted with EtOAc, the layers were separated and the EtOAc was evaporated to afford the title compound (0.037 g, 41%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.74 (br. s., 1H), 7.44 (d, 1H), 7.17 (d, 1H), 7.11 (s, 1H), 6.96 (dd, 1H), 4.19 (t, 2 H), 2.88 (t, 2H), 2.20 (s, 3H). LCMS: m/z=251.9 (M−1).

Provenance & Evidence