Pyridine → (4R,5R)-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

Participants

Reaction Steps

1-Chloroethyl chloroformate (1.55 mL, 14.2 mmol) was added dropwise to a stirred dichloromethane (50 mL) solution of (2R,3R)-6-hydroxyhexane-2,3-diyl dinitrate (intermediate 1, 2.60 g, 11.6 mmol), followed by pyridine (1.20 mL, 14.8 mmol). After 16 hours, the reaction mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel, eluting with 5-25% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.41 (q, J=5.7 Hz, 1H), 5.18-5.28 (m, 2H), 4.18-4.32 (m, 2H), 1.83 (d, J=5.7 Hz, 3H), 1.68-1.90 (m, 4H), 1.42 (d, J=6.4 Hz, 3H).

Provenance & Evidence