Tetrahydrofuran → HCID 54564561, compound

Participants

Reaction Steps

THF (100 ml) was added to 1,3-dioxan-2-ylethyltriphenylphosphinebromide (10.0 g, 21.9 mmol), followed by adding thereto potassium-t-butoxide (2.46 g, 21.9 mmol), stirring the mixture at the same temperature for 3 hours, dropwise adding to the reaction solution, a 20 ml THF solution of the above 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexane (5.7 g, 15.6 mmol), stirring the mixture at the same temperature for one hour, stirring for 3 hours at room temperature, adding water (100 ml) to the reaction solution, extracting the product with ethyl acetate, washing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, distilling off the solvent, purifying the resulting residue according to column chromatography treatment using heptane/ethyl acetate (3/1) as a developing solvent, on silica gel, distilling off the solvent, hydrogenating the residue (5.1 g) in the presence of a catalyst of 5% Pd/C (0.30 g) in an ethanol solution, filtering off the catalyst, distilling off the solvent under reduced pressure, and recrystallizing the residue from heptane/ethanol (5/1), to obtain 4-(4-(1,3-dioxan-2-ylethyl)cyclohexyl)-1-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexane (3.25 g, 6.94 mmol). The yield of this product from 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexane was 44.5%.

Provenance & Evidence