Dimethyl Sulfoxide → HCID 54287213, compound

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).

1. customquenched with 10% aqueous citric acid (50 mL)
2. extractionThe mixture was extracted into dichloromethane (3×50 mL)
3. washthe dichloromethane solution was washed with 10% aqueous citric acid (40 mL)
4. dry with materialdried over Na2SO4
5. customAfter removing the solvent in vacuo
6. customthe residue was purified by flash column chromatography (dichloromethane)

ORD record

ord-6989193945354433a29fe9849a0c414e

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05891909