Hydrochloric Acid → HCID 57448164, compound

Participants

Reaction Steps

To 1D (1.50 g, 4.67 mmol) in MeOH (23 mL) and water (5 mL) was added potassium carbonate (3.20 g, 23.4 mmol) and the reaction was refluxed for 45 min. After cooling to rt, the mixture was filtered and the filtrate was concentrated. The resulting residue was dissolved in ethyl acetate and washed with water and brine. The aqueous layer was back-extracted with ethyl acetate (5×). The combined organic layers were dried (MgSO4), filtered and concentrated to provide a yellow oil. The oil was dissolved in THF and 4N HCl in 1,4-dioxane (2.2 mL) was added. The resulting white solid was filtered to provide 1E (1.00 g). 1H NMR (400 MHz, CD3OD) δ ppm 1.03-1.21 (m, 2H), 1.30 (ddd, J=7.14, 4.50, 4.17 Hz, 2H), 2.80 (s, 3H), 2.84-3.03 (m, 1H), 2.86-3.05 (m, 1H), 4.41-4.65 (m, 2H), 7.59-7.93 (m, 3H), 8.06 (d, J=7.91 Hz, 1H). LC-MS: 226.10 (M+H)+.

Provenance & Evidence