18-Crown-6 → HCID 54495659, compound

Participants

Reaction Steps

1.62 g (0.014 mole) of potassium tert-butoxide was added to a solution of 1.02 g (0.0081 mole) of 4-fluorobenzyl alcohol and 0.12 g (0.00045 mole) of 18-crown-6 in 10 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 25 minutes. A solution of 0.60 g (0.0027 mole) of 7-chloro-1-(2-propenyl)-2,3-dimethylpyrrolo[2,3-d]pyridazine in 5 ml of tetrahydrofuran was added dropwise to the mixture and stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was poured into ice-water and the aqueous mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 2:3 mixture of ethyl acetate and hexane as an eluent to give 0.33 g of 7-(4-fluorobenzyloxy)-2,3-dimethyl-1-(1-propenyl)pyrrolo[2,3-d]pyridazine (trans) as a pale yellow powder.

Provenance & Evidence