Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl- → 3-[3-(4-Fluorophenyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]-3-oxopropyl]-benzonitrile
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][Si](C)(C)C)=[CH2:9])=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:33])[CH:23]=[CH:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])=[CH:18][CH:17]=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:9])[CH2:10][CH:24]([C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])[CH2:23][C:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)=[O:33])=[CH:4][CH:3]=1Participants
Procedure
1-Fluoro-4-[1-[(trimethylsilyl) oxy]ethenyl]-benzene (0.98 g, 2.86 mmol) is added to a cooled (-78° C.) solution of 3-[3-(4-fluorophenyl)-3-oxo-1-propenyl]-benzonitrile (0.6 g, 2.39 mmol) and TrSnCl5 (0.1 g, 0.19 mmol) in 70 mL of dichloromethane and stirred under nitrogen (N2) for 3 hours. The reaction mixture is diluted with additional dichloromethane, washed with a saturated solution of sodium bicarbonate, dried (MgSO4), and concentrated to an oil. The oil is taken up in 200 mL of diethyl ether and stirred with a few drops of tetrabutylammonium fluoride for 2 days. The diethyl ether is removed under vacuum and the residue columned over SiO2 eluting with dichloromethane. Pure fractions are combined, concentrated, and triturated in diethyl ether-hexane to provide 0.9 g of analytical material; mp 120°-123° C.
Workup
- washwashed with a saturated solution of sodium bicarbonate
- dry with materialdried (MgSO4)
- concentrationconcentrated to an oil
- customThe diethyl ether is removed under vacuum
- concentrationconcentrated
- customtriturated in diethyl ether-hexane
Sources & evidence
- ORD record
- ord-410ffae9fa654d8ab0212ec147542f7a
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430047
Reaction notes
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