Methanol → HCID 66747476, compound

Participants

Reaction Steps

Ethyl 3-[hydroxy(2-naphthyl)methyl]-5-pyridin-4-ylthiophene-2-carboxylate (70.0 mg, 0.180 mmol) was placed in a round bottomed flask equipped with a stirbar. Tetrahydrofuran (2.00 mL), methanol (1.00 mL), and water (1.50 mL) were added with stirring—all solids dissolved. Sodium hydroxide (1.0 M, 1.50 mL, 1.50 mmol) was added in a single portion and the resulting solution was stirred under an atmosphere of nitrogen overnight, resulting in a clear light yellow solution. The reaction was quenched into water and the pH of the mixture was adjusted the pH to ˜6-6.5 with sodium bicarbonate solution. The mixture was extracted with ethyl acetate, the extracts were combined and then rotovapped to leave crude product as a light yellow solid. The crude product was purified by HPLC to yield 9 mg (14% yield) product as a pale yellow powder. LC/MS (FA) ES+ 362. 1H NMR (400 MHz, DMSO) δ 8.60-8.51 (d, J=6.1 Hz, 2H), 7.98-7.94 (s, 2H), 7.91-7.75 (m, 4H), 7.68-7.58 (m, 3H), 7.53-7.37 (m, 2H), 6.64-6.36 (s, 1H).

Provenance & Evidence