Hydrochloric Acid → HCID 57910785, compound

Participants

Reaction Steps

Hydrochloric acid (100 mL of a 1.0 M solution in EtOH) was added to a stirred solution of 7b (15.8 g, 30.9 mmol) in EtOH (25.0 mL) at 0° C. After approximately 15 min, a second portion of hydrochloric acid (150 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 6.0 M aqueous solution) was added. After an additional 10 min, the reaction was warmed to rt and aged for 30 min. The reaction was diluted with water, recooled to 0° C. and 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 7c m/z (ES) 454 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.80 (d, 2H, J=4.8 Hz), 8.42 (d, 1H, J=3.0 Hz), 8.16 (d, 1H, J=8.7 Hz), 8.08 (d, 2H, J=8.5 Hz), 7.98 (d, 1H, J=8.9 Hz), 7.56 (d, 2H, J=8.5 Hz), 7.27 (m, 1H), 7.24 (dd, 1H, J=3.0, 8.7 Hz), 7.18 (d, 1H, J=8.9 Hz), 5.34 (s, 2H), 3.10 (m, 1H, J=6.7 Hz), 2.94 (s, 3H), 1.73 (s, 3H), 0.88 (d, 3H, J=6.7 Hz), 0.83 (d, 3H, J=6.8 Hz).

Provenance & Evidence