Sodium Hydroxide → (2R)-6-hydroxyhexane-1,2-diyl dinitrate

Participants

Reaction Steps

To a solution of (5R)-5,6-bis(nitrooxy)hexyl 4-nitrobenzoate (3.1 g, 8.3 mmol) in THF-EtOH (1:1, 0.5 M) at 0° C. was added sodium hydroxide 2N (10 mL, 20 mmol, 2 equiv) dropwise over 5 min. The reaction was stirred at rt for 2 h. The reaction mixture was quenched with a saturated NaHCO3 solution and extracted 3 times with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The product was purified by combi-flash 120 g silica gel cartridge using gradient (0-5% in 5 min, 5-55% in 30 min, 55-70% EA/Hex in 10 min) to afford the desired product (1.51 g, Yield=81%) as a colorless oil. 1H NMR (500 MHz, acetone-d6): δ 5.52-5.48 (m, 1H), 5.01 (dd, 1H), 4.72 (dd, 1H), 3.56-3.50 (m, 3H), 1.88-1.81 (m, 2H), 1.54-1.50 (m, 4H).

Provenance & Evidence