反应详情

温度

0 °C

Trans-4-butylcyclohexylacetyl chloride (25 g, 0.115 mol) was dissolved in dry tetrahydrofuran (30 ml), followed by cooling the solution down to 0° C., adding iron acetylacetonate (0.81 g), agitating the mixture, adding a solution of a Grignard reagent prepared from 1-bromo-3,4,5-trifluorobenzene (25 g, 0.115 mol) and metallic magnesium (2.8 g, 0.115 mol), in tetrahydrofuran, at a rate at which the reaction temperature did not exceed 10° C., reacting the mixture at 5° C. or lower for 2 hours, adding 6N hydrochloric acid (10 ml) and water (100 ml) to the reaction solution, extracting a deposited oily substance with n-heptane (100 m(), washing the extract solution with a dilute alkali aqueous solution, washing with water till the washing water became neutral, drying over anhydrous sodium sulfate, distilling off n-heptane from the n-heptane solution, and recrystallizing the residue from ethyl alcohol to obtain 1-(trans-4butylcyclohexylacetyl)-3,4,5-trifluorobenzene (21.0 g). C-I point: 42.8° C. This compound was dissolved in ethyl acetate (100 ml), followed by adding 5% Pd supported on barium sulfate (0.5 g), subjecting the mixture to a catalytic reduction at 25° C. under 3 atm till hydrogen absorption ceased, filtering off the catalyst after completion of the reaction, and subjecting the reaction solution to a suitable purification treatment to obtain 1-(trans-4-butylcyclohexyl)-2-(3,4,5-trifluorophenyl)ethane (18.0 g). C-I point: 8.4° C.

1. customdid not exceed 10° C.
2. customat 5° C.
3. extractionextracting a deposited oily substance with n-heptane (100 m(),
4. washwashing the extract solution with a dilute alkali aqueous solution
5. washwashing with water till the washing water
6. dry with materialdrying over anhydrous sodium sulfate
7. distillationdistilling off n-heptane from the n-heptane solution
8. customrecrystallizing the residue from ethyl alcohol