1,1-Dichloroethane → (5R)-1-chloro-5,6-bis(nitrooxy)hexyl propionate

Participants

Reaction Steps

Zinc chloride (1.3 g, 9.54 mmol) was added to a dichloroethane (11.9 mL) solution of (2R)-6-oxohexane-1,2-diyl dinitrate (530 mg, 2.39 mmol) and propionyl chloride (0.23 mL, 2.62 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium bicarbonate was added, and the solution was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica eluting with ethyl acetate/hexanes afforded the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.47 (d, J=5.0 Hz, 1H), 5.34-5.28 (m, 1H), 4.77 (dd, J=13.0, 3.5 Hz, 1H), 4.51 (dd, J=13.0, 6.5 Hz, 1H), 2.41 (q, J=7.5 Hz, 2H), 2.08 (q, J=7.5 Hz, 2H), 1.87-1.78 (m, 2H), 1.78-1.60 (m, 2H), 1.18 (t, J=7.5 Hz, 3H).

Provenance & Evidence