Tetrahydrofuran → 1-(4-Propylphenyl)-4-(4-oxocyclohexyl)-1-cyclohexene

Participants

Reaction Steps

Grignard reagent was prepared from 2.43 g (0.10 mol) of dried magnesium and 24.6 g (0.10 mol) of 4-propyliodobenzene in THF, and 100 ml of solution of 21.4 g (0.09 mol) of bicyclohexanedione monoethylene ketal in THF was added dropwise thereto and stirred at room temperature for 3 hours. The reaction solution was added in 300 ml of 3N hydrochloric acid, and the product thus formed was extracted with diethyl ether. After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn, the solvent was distilled off under a reduced pressure. To the residue were added 30 ml of toluene and 80 ml of formic acid, and the mixture was refluxed for 3 hours. To the reaction solution was added 100 ml of water and the product thus formed was extracted with toluene. After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn, the solvent was distilled off under a reduced pressure. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=4/1), the solvent was distilled off to give 9.5 g (32 mmol) of 1-(4-propylphenyl)-4-(4-oxocyclohexyl)-1-cyclohexene. Yield of this compound was 36%.

Provenance & Evidence