4-Oxo-1-phenylcyclohexanenitrile → 4-(5-Fluoropyridin-2-yl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

Participants

Reaction Steps

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.

Provenance & Evidence