Triacetoxyperiodinane → HCID 82283232, compound

To a stirred solution of 1-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)ethanol (0.34 g, 1.92 mmol) in DCM (40 mL) was added Dess-Martin periodinane (2.7 g, 6.5 mmol) at room temperature and the mixture stirred for 3 h. The reaction mixture was filtered and washed with DCM (15 mL). To the filtrate was added NaHCO3 solution (10 mL) and DCM (30 mL). The organic layer was separated, washed with water (20 mL) followed by brine solution (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get crude compound. The crude compound was purified by silica gel column chromatography (100-200 mesh; using 10% methanol in DCM) to obtain 1-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)ethanone as off-white solid (0.25 g, 72% yield). 1H NMR (400 MHz, CDCl3): δ 2.76 (s, 3H), 7.23 (t, 2H), 7.23 (dd, 2H), LC-MS m/z calculated for [M+H]+ 207.17, found 206.87.

1. filtrationThe reaction mixture was filtered
2. washwashed with DCM (15 mL)
3. additionTo the filtrate was added NaHCO3 solution (10 mL) and DCM (30 mL)
4. customThe organic layer was separated
5. washwashed with water (20 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customto get crude compound
9. customThe crude compound was purified by silica gel column chromatography (100-200 mesh; using 10% methanol in DCM)

ORD record

ord-c2ebec49c7274ec59e5a6a1c5b3bd5e8

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2