Sodium ethoxide → Benzonitrile,2-ethoxy-6-fluoro-4-(4-hydroxy-1-piperidinyl)-

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.200 g (0.839 mmol) of the above benzonitrile in EtOH (2 mL), cooled to 0° C., was added 1.0 mL (3.1 mmol) of sodium ethoxide. The reaction was heated to 70° C. for 15 h then cooled to room temperature and an additional 1.0 mL (3.1 mmol) of sodium ethoxide was added. The mixture was heated to 70° C. for an additional 15 h. The reaction was cooled to room temperature and excess base was consumed by the addition of a saturated aqueous solution of NH4Cl. The mixture was diluted with H2O and washed with CH2Cl2. The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide after 0.048 g (21%) of 2-ethoxy-6-fluoro-4-(4-hydroxy-piperidin-1-yl)-benzonitrile as a white solid.

Provenance & Evidence