Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[O:22]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)=[O:22])=[O:10])=[CH:6][CH:7]=1Komponenten
Versuchsvorschrift
To a stirred solution of 4.45 g (28.9 mmol) of 4-fluorophenylacetic acid in 3.26 g (31.8 mmol) of triethylamine and 275 mL of acetonitrile was added 8.9 g (28.9 mmol) of 2-bromo-4'-(methylsulfonyl)acetophenone (prepared in Step 3) at ambient temperature. The reaction mixture was stirred for 30 minutes, concentrated in vacuo, and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography with ethyl acetate/hexane (1:1) gave 6.87 g (68%) of 2-(4-fluorophenyl)-1-[2-[4-(methylsulfonyl) phenyl]-2-oxoethoxy]ethanone as a colorless solid: NMR (CDCl3) δ 3.08 (s, 3H), 3.79 (s, 2H), 5.35 (s, 2H), 7.06 (s, t, J=9 Hz, 2H), 7.32 (dd, J=6and 9 Hz, 2H), 8.06 (s, 4H).
Aufarbeitung
- concentrationconcentrated in vacuo
- custompartitioned between ethyl acetate and water
- dry with materialThe organic phase was dried (MgSO4)
- concentrationconcentrated in vacuo
- customPurification by silica gel chromatography with ethyl acetate/hexane (1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-3377be980e814afb9b03c36ff6557afe
- Quelldatensatz
- uspto-grants-1995_02
- Patentnummer
- US05393790
Verknüpfte Notizen
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