Acetic Acid → HCID 24993419, compound

Participants

Reaction Steps

A mixture of the product of Step B (56 mg, 0.11 mmol), hydrazine (6.6 μL, 0.21 mmol), and AcOH (12.0 μL, 0.21 mmol) in 5.0 mL of EtOH was refluxed for 16 h. The reaction mixture was then cooled to rt, diluted with Et2O (50 mL), and washed with saturated aq NaHCO3 (2×50 mL) and brine (50 mL). After phase separation, the organic phase was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 2:3 v/v acetone/hexanes as the eluant afforded the title compound: 1H NMR δ 1.48 (s, 3H), 1.54 (s, 3H), 1.82 (t, J=12.4, 1H), 2.26 (s, 3H), 2.41 (dd, J=5.9, 13.3, 1H), 3.86 (br. s, 1H), 4.92 (m, 1H), 5.45 (s, 1H), 7.00 (d, J=8.4, 2H), 7.15-7.26 (m, 5H), 7.97 (s, 1H).

Provenance & Evidence