Dimethyl Sulfoxide → HCID 18786390, compound

Temperature

-78 °C

A solution of [4-[3-[4-(2-methylimidazol-1-yl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-yl]methanol (230 mg, 0.6 mmol) in dichloromethane (5 ml) was added dropwise to the Swern reagent [1.2 mmol, 2 equiv., prepared by adding a solution of DMSO (143 mg) in dichloromethane (5 ml) to a solution of oxalyl chloride (155 mg, 1.2 mmol) in dichloromethane (10 ml) at -78° C.] under argon at -78° C. The reaction mixture was stirred for 0.5 h at -78° C. and then this was allowed to warm to -20° C. over 2 h. To the reaction mixture was added triethylamine (1 ml) and the resulted solution was stirred for 0.5 h at 0° C. The mixture was partitioned between saturated aqueous NH4Cl (50 ml) and ethyl acetate (50 ml), the organic phase was separated and the aqueous phase was extracted with ethyl acetate (20 ml×2). The combined organic extracts were washed with water (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo. The residual oil was purified by column chromatography {SiO2, 100 g; eluted with dichloromethane/ethanol (20/1)} to afford 178 mg (77%) of the titled compound as white solids.

1. customprepared
2. temperatureto warm to -20° C. over 2 h
3. stirringthe resulted solution was stirred for 0.5 h at 0° C
4. customThe mixture was partitioned between saturated aqueous NH4Cl (50 ml) and ethyl acetate (50 ml)
5. customthe organic phase was separated
6. extractionthe aqueous phase was extracted with ethyl acetate (20 ml×2)
7. washThe combined organic extracts were washed with water (50 ml) and brine (50 ml)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. customThe residual oil was purified by column chromatography {SiO2, 100 g
11. washeluted with dichloromethane/ethanol (20/1)}

ORD record

ord-2f97d4eba9ad49f78f0e9de64f6d1bc4

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05883106