Dimethyl Sulfoxide → HCID 54287213, compound

Participants

Reaction Steps

Sulfur trioxide pyridine complex (720 mg, 4.5 mmol) was added to a solution of 3-[5-methyl-3-(3-methylphenylsulfonyloxy)phenoxy]propanol (505 mg, 1.5 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.6 mL, 4.7 mmol) and anhydrous dimethyl sulfoxide (0.3 mL, 4.2 mmol) in anhydrous dichloromethane (15 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (50 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 (450 mg, 89%). 1H-NMR (300 MHz, CDCl3) δ 9.83 (s, 1H), 7.69 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.46 (t, J=7.7 Hz, 1H), 7.41 (t, J=7.6 Hz, 1H), 6.61 (s, 1H), 6.44 (s, 1H), 6.35 (s, 1H), 4.18 (t, J=6.0 Hz, 2H), 2.85 (t, J=6.1 Hz, 2H), 2.43 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence