1-(Triphenylphosphoranylidene)acetone → 3-Buten-2-one,4-(4-CF3-phenyl)-

4-(Trifluoromethyl)benzaldehyde (25.0 g, 144 mmol) was taken up in 500 mL of DCM. 1-Triphenylphosphoranylidene-2-propanone (48.0 g, 151 mmol) was added. After 5 hours, an additional 3 g of 1-triphenylphosphoranylidene-2-propanone was added. The mixture was stirred for 10 hours. The solvent was removed under reduced pressure, and the residue was triturated with 500 mL of 5% EtOAc/hexanes. The mixture was filtered, removing a large amount of P(O)Ph3. The residue was taken up in 300 mL of 2.5% EtOAc/hexanes and filtered through a pad of silica. The mixture was concentrated under reduced pressure and the residue was found to be (E)-4-(4-(trifluoromethyl)phenyl)but-3-en-2-one (28.3 g, 92.0% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.68-7.60 (m, 4H), 7.52 (d, J=16.43 Hz, 1H), 6.78 (d, J=16.4 Hz, 1H), 2.41 (s, 3H).

1. customThe solvent was removed under reduced pressure
2. customthe residue was triturated with 500 mL of 5% EtOAc/hexanes
3. filtrationThe mixture was filtered
4. customremoving a large amount of P(O)Ph3
5. filtrationfiltered through a pad of silica
6. concentrationThe mixture was concentrated under reduced pressure

ORD record

ord-25b3f4ccb2214ee098ef1d61cb52fc46

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084479B2