Phosphoric Acid → HCID 10255058, compound

Participants

Reaction Steps

To a solution of 4.3 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-4-oxo-3-phenylbut-2-enyl 6-(nitrooxy)hexanoate in a solvent mixture of 50 mL of THF with 50 mL of t-BuOH, 5 mL of 2-methyl-2-butene was added followed by the addition of 20 mL of 2 M phosphoric acid and 20 mL of 1 M of NaClO2. The resulting mixture was stirred at rt for 15 min. The organic phases were separated and the aqueous phase was extracted with EtOAc. The organic phases were combined, dried over Na2SO4, filtered, and then evaporated. The crude was purified by flash chromatography over silica gel (5–100% EtOAc/hexane) to afford 3.8 g of the titled compound as white solid. 1H NMR (acetone-d6, 500 M Hz): δ 7.79 (d, 2H), 7.45 (d, 2 H), 7.22–7.15 (m, 3 H), 7.15–7.10 (m, 2 H), 5.31 (s, 2 H), 4.51 (t, 2 H), 3.07 (s, 3 H), 2.23 (t, 2 H), 1.72–1.65 (m, 2 H), 1.52–1.45 (m, 2 H), 1.37–1.29 (m, 2 H).

Provenance & Evidence