Phosphoric Acid → HCID 10052418, compound

Participants

Reaction Steps

A solution of 4.5 g of (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl 6-(nitrooxy)hexyl carbonate in 100 mL of dichloromethane was treated with 4.5 g of Dess-Martin reagent at 25° C. for 75 min. The reaction was quenched by 1 mL of water, and stirred at RT for 30 min. Then the mixture was filtered through a pad of silica gel and evaporated. The crude thus obtained was dissolved in a solvent mixture of THF and t-BuOH (100 mL/100 mL). To the resulting solution was added 5.3 mL of 2-methyl-2-butene followed by the addition of 13 mL of phosphoric acid (1.2 M soln) and 13 mL of NaClO2 (1M soln). The resulting mixture was stirred at RT for 30 min. The organic phase was 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 to afford titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 11.8 (bs, 1 H), 7.76 (d, 2 H), 7.43 (d, 2 H), 7.17–7.11 (m, 5 H), 5.34 (s, 2 H), 4.52 (t, 2 H), 4.04 (t, 2 H), 3.05 (s, 3 H), 1.71 (m, 2 H), 1.57 (m, 2 H), 1.40 (m, 2 H), 1.34 (m, 2 H).

Provenance & Evidence