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

Participants

Reaction Steps

Sulfur trioxide pyridine complex (847 mg, 5.36 mmol) was added to a solution of 619 mg (1.74 mmol) of 3-[3-(2-chlorophenylsulfonyloxy)-5-methylphenoxy]propanol, as prepared in the preceding step, 411 μL (3.23 mmol) of N,N-diisopropylethylamine, and 230 μL (3.0 mmol) of anhydrous dimethyl sulfoxide in anhydrous dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 h and then quenched with 10% aqueous citric acid (20 mL). The reaction mixture was extracted with diethyl ether (3×30 mL), dried (MgSO4), and purified by flash chromatography (diethyl ether/petroleum ether (2:1 to 4:1)) to afford 289 mg (47% yield) of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 9.83 (t, 1 H, J=1.4 Hz), 7.97 (dd, 1 H), 7.56-7.65 (m, 2 H), 7.35-7.42 (m, 1 H), 6.60 (br s, 1 H), 6.57 (br s, 1 H), 6.49 (br s, 1 H), 4.19 (t, 2 H, J=6.1 Hz), 2.86 (td, 2 H, J=1.4, 6 Hz), and 2.25 (s, 3 H).

Provenance & Evidence