Dimethyl Sulfoxide → HCID 54256661, compound

Temperature

0 °C

To a cooled (0° C.), stirred solution of 528 mg (1.44 mmol) of 3-[3-(5-fluoro-2-methylphenylsulfonyloxy)-5-methylphenoxy]propanol, as prepared in the preceding step, 527 μL (3.02 mmol) of N,N-diisopropylethylamine and 307 μL (4.32 mmol) of anhydrous dimethyl sulfoxide in 6.0 mL of anhydrous dichloromethane was added 459 mg (2.88 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 3% ethyl acetate-dichloromethane to afford 320 mg (61%) of the title compound as a colorless syrup: Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C17H17FO5S: 375.1 (M+Na). Found: 375.0.

1. additionwas added 459 mg (2.88 mmol) of sulfur trioxide pyridine complex
2. temperatureThe mixture was warmed to ambient temperature over 30 min
3. washwashed with 5% (w/v) aqueous citric acid (2×25 mL)
4. extractionEach wash was extracted with 5 mL of dichloromethane
5. washthe combined extracts were washed with brine (25 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe resulting material was chromatographed on 35 g of silica gel with dichloromethane

ORD record

ord-835f811b5b0a49bfbf5c5708e057345f

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05891909