Gamma-Valerolactone → Pentanamide, N-heptyl-5-hydroxy-

Participants

Reaction Steps

Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL), washed with 1 N aqueous HCl (50 mL), water and brine. The organic layer was dried over magnesium sulfate and concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-56°. 1H NMR (CDCl3) δ6.06 (bs, 1H), 3.61 (t,2H, J=7.3 Hz), 3.24 (quartet,2H,J=8.4 Hz), 3.19 (bs, 1H), 2.19 (t,2H, J=8.3 Hz), 1.80-1.23 (m, 14H), 0.86 (t,3H, J=6.0 Hz).

Provenance & Evidence