4-Oxo-1-phenylcyclohexanenitrile → 4-(5-Fluoropyridin-2-yl)-4-hydroxy-1-phenylcyclohexanecarbonitrile
Reaktionsgleichung
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[O:9]=[C:10]1[CH2:15][CH2:14][C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:16]#[N:17])[CH2:12][CH2:11]1>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2([OH:9])[CH2:15][CH2:14][C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:16]#[N:17])[CH2:12][CH2:11]2)=[N:3][CH:4]=1Komponenten
3
Versuchsvorschrift
According to the process described in Example 260, 25 mmol of 2-bromo-5-fluoropyridine were converted into the Grignard reagent and reacted with 25 mmol of 4-oxo-1-phenylcyclohexanecarbonitrile (dissolved in 100 ml of THF). The chromatographic separation of the crude product (silica gel flash column; HEP/EA 3:1) afforded two main fractions (TLC (HEP/EA 1:1): Rf 0.58 and 0.49), which were combined. 6.6 g of the title compound (cis/trans mixture) were obtained as a viscous yellow oil.
Aufarbeitung
- customThe chromatographic separation of the crude product (silica gel flash column; HEP/EA 3:1)