3,5-Dimethylpyrazole → 3,5-dimethyl-1-octyl-1H-pyrazole

Participants

Reaction Steps

1-Octyl-3,5-dimethylpyrazole was prepared in the following manner. All manipulations were performed under a nitrogen atmosphere. 3,5-Dimethylpyrazole (5 g) was placed in a 100-mL 3-neck round-bottom flask with a magnetic stir bar and dissolved in 50 mL tetrahydrofuran. A condenser and stoppers were added. Sodium metal (1.2 g) was added in pieces. Hydrogen evolution was evident. Mixture was stirred at room temperature overnight. 1-Bromooctane (9 mL) was then added all at once. The mixture was brought to a gentle reflux for seven hours and then stirred overnight at room temperature. The reaction mixture was filtered through a sintered-glass frit to remove a white precipitate. Solvent was removed under vacuum. Product was distilled under vacuum. The fractions distilling at 65-70° C. were collected and used in subsequent preparations.

Provenance & Evidence