Dimethyl Sulfoxide → HCID 57208440, compound

Participants

Reaction Steps

Sulfur trioxide pyridine complex (1.0 g, 6.5 mmol) was added to a solution of 3-[3-(2-cyano-5-methylphenylsulfonyloxy)-5-methylphenoxy]-propanol (720 mg, 2.0 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.7 mL, 5.5 mmol) and anhydrous dimethyl sulfoxide (0.4 mL, 5.6 mmol) in anhydrous dichloromethane (20 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (60 mL). The mixture was extracted into dichloromethane (3×50 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (40 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a colorless oil (520 mg, 72%). 1H-NMR (300 MHz, CDCl3) δ 9.81 (s, 1H), 7.89 (s, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.55 (d, J=7.9 Hz, 1H), 6.62 (s, 1H), 6.60 (s, 1H), 6.56 (s, 1H), 4.22 (t, J=6.0 Hz, 2H), 2.85 (t, J=6.0 Hz, 2H), 2.49 (s, 3H), 2.25 (s, 3H).

Provenance & Evidence