Formic Acid → HCID 21993278, compound

Participants

Reaction Steps

1-(2-(1,3-Dioxane-2-yl)ethyl)cyclohexyl-3,4,5-trifluorobenzene 3.7 g (11 mmol) obtained in Example 8 and formic acid 25.0 g (540 mmol) were added to toluene 20 ml, and the mixture was refluxed with heating for 3 hours. The reactant was cooled to room temperature, water 100 ml was added, and the product was extracted with toluene. The extract was washed with water, a saturated sodium bicarbonate aqueous solution, and water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain crude 3-(4-(3,4,5-trifluorophenyl)cyclohexyl)propanal 3.5 g. The product and 2-propyl-1,3-propanediol 2.3 g (20 mmol) were dissolved in toluene 20 ml, PTS 0.5 g was added. The mixture was refluxed with heating for 3 hours while removing water formed with Dien-Stark. The reactant was washed with a saturated sodium bicarbonate aqueous solution, and then with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized twice from ethanol to obtain 1-(2-(5-propyl-1,3-dioxane-2-yl)ethyl)cyclohexyl-3,4,5-trifluorobenzene 1.4 g (3.8 mmol). The yield was 34.5% from 1-(2-(1,3-dioxane-2-yl)ethyl)cyclohexyl-3,4,5-trifluorobenzene.

Provenance & Evidence