反应详情

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.

1. additionby dropwise adding
2. extractionextracting the resulting product with toluene
3. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
4. dry with materialdrying over magnesium sulfate
5. distillationdistilling off the solvent
6. custompurifying the residue
7. distillationon silica gel, distilling off the solvent
8. customrecrystallizing the residue from ethanol/heptane (9/1)