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

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).

1. extractionthe solution was extracted with dichloromethane
2. dry with materialThe combined organic layers were dried (magnesium sulfate)
3. filtrationfiltered
4. concentrationconcentrated in vacuo

ORD record

ord-e9542366a9cb4c0e97f9e5d3e801577b

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880014B2