Dimethyl Sulfoxide → HCID 57297888, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred solution of 360 mg (0.941 mmol) of 3-[3-(2,5-dimethoxyphenylsulfonyloxy)-5-methylphenoxy]propanol, as prepared in the preceding step, 344 μL (1.98 mmol) of N,N-diisopropylethylamine and 200 μL (2.82 mmol) of anhydrous dimethyl sulfoxide in 6.0 mL of anhydrous dichloromethane was added 300 mg (1.88 mmol) of sulfur trioxide pyridine complex. The mixture was warmed to ambient temperature over 30 min and stirred for 16 h. The mixture was then poured into 15 mL of dichloromethane and washed with 5% (w/v) aqueous citric acid (2×25 mL). Each wash was extracted with 5 mL of dichloromethane and the combined extracts were washed with brine (25 mL), dried over Na2SO4 and concentrated. The resulting material was chromatographed on 35 g of silica gel with dichloromethane followed by 2.5% ethyl acetate-dichloromethane to afford 268 mg (75%) of the.title compound as a colorless resin: 1H-NMR (300 MHz; CDCl3) δ 9.83 (t, 1 H, J=1.4 Hz), 7.34 (d, 1 H, J=3.1 Hz), 7.15 (dd, 1 H, J=9.1, 3.1 Hz), 7.03 (d, 1 H, J=9.1 Hz), 6.59 (m, 1 H), 6.56 (m, 1 H), 6.47 (t, 1 H, J=2.1 Hz), 4.20 (t, 2 H, J=6.1 Hz), 3.97 (s, 3 H), 3.76 (s, 3 H), 2.86 (td, 2 H, J=6.1, 1.4 Hz), and 2.25 (s, 3 H).

Provenance & Evidence