Acetic Acid → HCID 68194936, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 163A (1.45 g, 4.00 mmol) in 95% ethanol (20 mL) were added zinc (2 g, 30.6 mmol) and acetic acid (4 mL, 69.9 mmol). The reaction mixture was stirred for 4 hours at 50° C. Aqueous saturated NaHCO3 solution (200 mL) and CH2Cl2 (200 mL) were added to the reaction mixture and the suspension was filtered. The aqueous layer was extracted with CH2Cl2 (200 mL). The combined organic layers were washed with saturated NaCl (1×300 mL), dried over Na2SO4, filtered, and concentrated. The crude material was purified using the Chemflash system using a 120 g C18 column eluting with 40-80% methanol in water (0.8 g (NH4)2CO3 in 1 L of water) to provide the title compound. LC-MS: m/e=333 (M+H)+. 1H NMR (400 MHz, DMSO-d6), δ 8.25 (s, 1H), 7.73 (s, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.11 (s, 1H), 6.97 (d, J=8.4 Hz, 1H), 6.41 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.16 (d, J=2.0 Hz, 1H), 4.76 (s, 2H), 3.62 (s, 2H), 3.43 (s, 2H), 2.31 (s, 2H), 1.15 (s, 6H).

Provenance & Evidence