Benzyl Bromide → HCID 11467790, compound

Participants

Reaction Steps

To 300 mg of (2Z)-4-({[2,3-bis(nitrooxy)propoxy]carbonyl}oxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 5 mL of DMF was added 69 μL benzyl bromide followed by 81 mg of potassium carbonate (325 mesh). The resulting mixture was stirred at rt for 30 min. The reaction was then quenched with saturated solution of NH4Cl and extracted with Et2O/hexanes (½, 2 times). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give a pale yellow residue. Flash chromatography of the crude material over silica gel (10-70% EtOAc/hexane) afforded 250 mg of the title compound as a white solid. 1H NMR (500 μL, acetone-d6): δ 7.80 (d, 2H), 7.48 (d, 2H), 7.42-7.35 (m, 5H), 7.21-7.18 (m, 3H), 7.13-7.10 (m, 2H), 5.77-5.73 (m, 1H), 5.36 (s, 2H), 5.33 (s, 2H), 5.04 (dd, 1H), 4.84 (dd, 1H), 4.64 (dd, 1H), 4.48 (dd, 1H), 3.08 (s, 3H).

Provenance & Evidence