4-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzonitrile → 4-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzonitrile
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:33])[C:21]=1[O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH2:5][CH:6]([CH2:17][OH:18])[CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:33])[C:21]=1[O:22][Si:23]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:31])[CH3:32])[CH2:5][CH:6]([CH:17]=[O:18])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 750 mg (1.58 mmol) of 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzonitrile in 9 ml of dichloromethane is mixed with 409 mg (1.9 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 h. After conversion is complete, about 10 g of silica gel are added, and the solvent is removed in vacuo to dryness. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→5:1→2:1). 493 mg (64% of theory) of a colorless solid are obtained.