(Diethylamino)sulfur trifluoride → HCID 21459479, compound

Participants

Reaction Steps

Dimethoxyethane (10 ml) was added to the above 3-(4-(4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)propanol (1.20 g, 3.03 mmol), followed by dropwise adding thereto diethylaminosulfur trifluoride (DAST) (1.13 g, 7.01 mmol), refluxing the mixture for 5 hours, extracting the resulting product with toluene, 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 residue according to column chromatography treatment using heptane as a developing solvent, on silica gel, distilling off the solvent, and recrystallizing the residue from ethanol/heptane (9/1), to isolate only trans-form of 1-(2-(4-(4-(3-fluoropropyl)cyclohexyl)cyclohexyl)ethyl)-4-trifluoromethylbenzene (0.60 g, 1.5 mmol). Yield: 49.5%. SB -I point: 118.9° C.

Provenance & Evidence