Potassium Carbonate → HCID 71226788, compound

To a round bottom flask was added K2CO3 (5.09 g, 36.8 mmol), 1-(isocyanomethylsulfonyl)-4-methylbenzene (3.95 g, 20.25 mmol), MeOH (30 mL) and 4-(trifluoromethoxy)benzaldehyde (2.63 mL, 18.41 mmol). The reaction was refluxed for 2 hrs. After this time, the reaction mixture was concentrated under reduced pressure. The remaining residue was dissolved in water (50 ml). The aqueous solution was extract with EtOAc (50 ml). The EtOAc layer was washed with saturated aqueous NaCl (30 ml), dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give the product, 5-(4-(trifluoromethoxy)phenyl)oxazole, (3.5 g, 15.27 mmol, 83% yield) as an off white solid. Anal. Calcd. for C10H6F3NO2 m/z 229.1, found: 230.1 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.94 (s, 1H), 7.70 (d, J=8.80 Hz, 2H), 7.37 (s, 1H), 7.29 (d, J=8.25 Hz, 2H).

1. temperatureThe reaction was refluxed for 2 hrs
2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
3. dissolutionThe remaining residue was dissolved in water (50 ml)
4. extractionThe aqueous solution was extract with EtOAc (50 ml)
5. washThe EtOAc layer was washed with saturated aqueous NaCl (30 ml)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting residue was purified
10. washeluting with a gradient of 0-100% EtOAc/Hex

ORD record

ord-9268c0f71b31437da948a891eb242f4a

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815909B2