Tetrahydrofuran → 4-(3,4,5-Trifluorophenyl)cyclohexane-1-carbaldehyde

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Reaction Steps

To dried methoxymethyltriphenylphosphonium chloride (abbreviated as MTP, hereinafter) 25 g (72.9 mmol), THF 300 ml was added, and potassium-t-butoxide 8.2 g (73.1 mmol) was added. The mixture was stirred for about one hour. To the reactant, a THF solution (150 ml) of the above 4-(3,4,5-trifluorophenyl)cyclohexanone 14.8 g (64.9 mmol) was added dropwise, and the mixture was stirred for 2 hours. Water 300 ml was added to the reactant, the product was extracted with toluene. 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 acid 200 ml and THF 200 ml for 5 hours, 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-(3,4,5-trifluorophenyl) cyclohexanecarboaldehyde 10.5 g (43.3 mmol). The yield was 66.7% from 4-(3,4,5-trifluorophenyl) cyclohexanone.

Provenance & Evidence