Dimethyl Sulfoxide → 3-[5-Methyl-3-(2-trifluoromethylbenzyloxy)phenoxy]propionaldehyde

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Reaction Steps

Sulfur trioxide pyridine complex (1.3 g, 8.0 mmol) was added to a solution of 3-[5-methyl-3-(2-trifluoromethylbenzyloxy)phenoxy]propanol (680 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 (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 white solid (575 mg, 85%). 1H-NMR (300 MHz, CDCl3) δ 9.85 (s, 1 H), 7.75 (d, J=7.8 Hz, 1 H), 7.69 (d, J=7.8 Hz, 1 H), 7.56 (t, J=7.6 Hz, 1 H), 7.41 (t, J=7.6 Hz, 1 H), 6.42 (s, 1H), 6.37 (s, 1 H), 6.35 (s, 1 H), 5.23 (s, 2 H), 4.27 (t, J=6.1 Hz, 2 H), 2.87 (t, J=6.1 Hz, 2 H), 2.29 (s, 3 H).

Provenance & Evidence