Tetrahydrofuran → HCID 21993293, compound

Participants

Reaction Steps

To dried MTP 10.0 g (29.2 mmol), THF 100 ml was added, and potassium-t-butoxide 3.30 g (29.4 mmol) was added. The mixture was stirred for about one hour. To the reactant, a THF solution (50 ml) of the above 4-(3,5-difluorophenyl)cyclohexanone 5.0 g (23.8 mmol) was added dropwise, and the mixture was stirred for 2 hours. Water 150 ml was added to the reactant, the product was extracted with diethylether. The extract was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene). The resulting purified material was stirred in mixture solvent of 3N-hydrochloric add 200 ml and acetone 200 ml for 5 hours at room temperature, and the product was extracted with toluene. The extract was washed with a saturated sodium bicarbonate aqueous solution and then with water, and dried over anhydrous magnesium sulfate. Toluene was distilled off to obtain 4-(3,5-difluorophenyl)cyclohexanecarboaldehyde 5.0 g (22.3 mmol). The yield was 93.7% from 4-(3,5-difluorophenyl) cyclohexanone.

Provenance & Evidence