Hydrochloric Acid → HCID 59393652, compound

Participants

Reaction Steps

Hydrochloric acid (100 mL of a 1.0 M solution in EtOH) was added to a stirred solution of 4y (7.03 g, 12.3 mmol) in EtOH (50.0 mL) at 0° C. After approximately 15 min, a second portion of hydrochloric acid (100 mL of a 2.0 M aqueous solution) was added, and after another 15 min, a third portion of hydrochloric acid (100 mL of a 1.0 M solution in EtOH). After an additional 15 min, a final portion of hydrochloric acid (50 mL of a 6.0 M aqueous solution) was added, and the resulting reaction was aged for 30 min. The reaction was carefully neutralized by the addition of solid sodium bicarbonate. The resulting mixture was saturated with solid sodium chloride and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 4z m/z (ES) 517 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.32 (d, 1H, J=2.3 Hz), 8.95 (s, 2H), 8.47 (dd, 1H, J=2.3, 8.5 Hz), 8.22 (d, 1H, J=8.9 Hz), 8.04 (d, 1H, J=8.9 Hz), 7.58 (m, 4H), 7.50 (d, 1H, J=8.4 Hz), 5.91 (s, 2H), 3.24 (m, 1H), 2.94 (s, 3H), 2.37 (s, 6H), 1.82 (s, 3H), 0.94 (d, 3H, J=6.6 Hz), 0.89 (d, 3H, J=6.6 Hz).

Provenance & Evidence