1-(Triphenylphosphoranylidene)acetone → 3-Buten-2-one,4-(4-CF3-phenyl)-
反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21](=[O:23])[CH3:22])C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:20]/[C:21](=[O:23])[CH3:22])=[CH:5][CH:4]=1参加物
4
実験手順
4-(Trifluoromethyl)benzaldehyde (25.0 g, 144 mmol)(commercially available from 3B Scientific Corporation Product List (Order Number 3B4-3644)) 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 the Wittig reagent 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, 3H), 7.52 (d, J=16.43 Hz, 1H), 6.78 (d, J=16.4 Hz, 1H), 2.41 (s, 3H).