Phosphoric Acid → {([2,3-Bis(nitrooxy)propoxy]carbonyl}oxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid

Participants

Reaction Steps

To a solution of 3.1 g of 2,3-bis(nitrooxy)propyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate in 30 mL of dichloromethane was added 3.1 g of Dess-Martin reagent and the resultant mixture was stirred at rt for 2 h. Then 3 mL of water was added and the resultant mixture was stirred at rt for 0.5 h. The cloudy mixture was then filtered and filtrate extracted 3× with EtOAc. The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo to give a pale yellow residue. The crude material was then dissolved in a solvent mixture of 5 mL of THF with 5 mL of t-BuOH and to this was added 2 mL of 2-methyl-2-butene followed by the addition of 2 mL of 1 M of phosphoric acid and 1.16 g of NaClO2. The reaction mixture was stirred at rt for 3.5 h. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layer was dried (Na2SO4), filtered, and then concentrated in vacuo. The crude was purified by recrystallization from warm ether to afford 1.23 g of the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 7.79 (d, 2H), 7.47 (d, 2H), 7.22-7.14 (m, 5H), 5.75-5.72 (m, 1H), 5.43 (s, 2H), 5.03 (dd, 1H), 4.83 (dd, 1H), 4.63 (dd, 1H), 4.47 (dd, 1H), 3.08 (s, 3H).

Provenance & Evidence