HCID 10163059, compound → HCID 10162253, compound

Participants

Reaction Steps

To a solution of 5-[6-(3-[1-adamantyl]-4-methoxyphenyl)-naphthalen-2-yl]-2,4-thiazolidinedione (0.130 g, 0.27 mmol) in 10 mL of anhydrous CH2Cl2 cooled to −78° C. under argon was added borontribromide (0.31 mL, 3.23 mmol). The cooling bath was removed and the reaction mixture was stirred for 18 hours at RT. The resulting mixture was carefully poured onto ice and extracted with CH2Cl2 (2×50 mL). The combined organics were washed with water, brine and dried over magnesium sulfate. The mixture was filtered, evaporated and the residue was purified on silica gel (eluent: hexane:EtOAc, 3:2) to give 5-[6-(3-[1-adamantyl]-4-hydroxyphenyl)-naphthalen-2-yl]-2,4-thiazolidinedione as a solid (0.090 g, 72% yield); mp 312–314.5° C., 1H NMR (300 MHz; DMSO-d6): δ 1.74 (s, 6H), 2.05–2.15 (m, 9H), 5.97 (s, 3H), 6.88 (d, J=8.1 Hz, 1H), 7.43–7.51 (m, 3H), 7.81 (dd, J1=8.7 Hz, J2=1.8 Hz 1H), 7.94–8.02 (m, 3H), 8.10 (s, 1H), 9.52 (s, 1H), 12.35 (brs, 1H).

Provenance & Evidence