Dimethyl Sulfoxide → 3-[3-(2,5-Dimethylphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde

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Reaction Steps

Sulfur trioxide pyridine complex (800 mg, 5.0 mmol) was added to a solution of 3-[3-(2,5-dimethylphenylsulfonyloxy)-5-methylphenoxy]propanol (600 mg, 1.7 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 (530 mg, 89%). 1H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1H), 7.68 (s, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.29 (s, 1H), 6.60 (s, 1H), 6.45 (s, 1H), 6.35 (s, 1H), 4.17 (t, J=6.1 Hz, 2H), 2.85 (t, J=6.1 Hz, 2H), 2.70 (s, 3H), 2.33 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence