Acetic Acid → HCID 66738409, compound

Participants

Reaction Steps

In a 50 mL round-bottom flask fitted with a stirring bar, reflux condenser, 0.196 g Lactone 2 (1.125 mmol), and propylamine (0.83 ml, 0.6 g, 10.13 mmol) were combined, then glacial acetic acid (0.19 ml, 0.20 g, 3.36 mmol) was added. The solution was warmed to 85° C. in an oil bath for 30 min, at which time TLC(CHCl3:MeOH:NH3OH=100:10:1) indicated complete consumption of the starting lactone. Reaction mixture was purified by flash column with the same solvent as TLC. Product 3 was collected, yielding 206 mg (80% yield). Mp: 132-133° C., Rf 0.03 (CHCl3:MeOH:NH3OH=100:10:1); MS: [M-H]−=232; 1H NMR (300 MHz, DMSO) δ 0.81 (t, J=6.0 Hz, 3H), 1.41 (ddd, J=13.8, 7.5, 6.9 Hz, 2H) 1.66-1.83 (m, 4H), 3.02 (dd, J=6.9, 6.6 Hz, 2H), 3.22 (t, J=6.0 Hz, 1H), 3.75 (ddd, J=13.8, 9.0, 5.7 Hz, 1H), 3.94 (s, 1H), 4.69 (d, J=4.5 Hz, 1H), 4.90 (d, J=5.4 Hz, 1H), 5.19 (d, J=3.6 Hz, 1H), 5.47 (s, 1H), 7.76 (t, J=5.4 Hz, 1H).

Provenance & Evidence