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

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).

1. customThe reaction mixture was quenched with a saturated NaHCO3 solution
2. extractionextracted 3 times with EtOAc
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated
7. customThe product was purified by combi-flash 120 g silica gel cartridge
8. custom(0-5% in 5 min, 5-55% in 30 min, 55-70% EA/Hex in 10 min)

ORD record

ord-0f4876c49cba48fca0cda883d2803479

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622502B2