Dimethyl Sulfoxide → HCID 54268437, compound

Participants

Reaction Steps

Sulfur trioxide pyridine complex (1.10 g, 7.0 mmol) was added to a solution of 3-[3-(3-cyanophenylsulfonyloxy)-5-methylphenoxy]propanol (1.05 g, 3.0 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 (80 mL). The mixture was extracted into dichloromethane (3×60 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (50 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 (770 mg, 74%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (s, 1H), 8.14 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.72 (t, J=7.9 Hz, 1H), 6.65 (s, 1H), 6.42 (s, 1H), 6.37 (s, 1H), 4.21 (t, J=6.0 Hz, 2H), 2.89 (t, J=6.0 Hz, 2H), 2.27 (s, 3H).

Provenance & Evidence