反应详情

温度

-10 °C

Commercially available methoxymethyltriphenylphosphonium chloride (257 g, 0.75 mol) was added to tetrahydrofuran (500 ml), followed by adding potassium t-butoxide (84.2 g, 0.75 mol) in argon atmosphere with stirring at -10° C. over 40 minutes, agitating the reaction solution at 0° C. for one hour, dropwise adding a solution of 3-[trans-4-(4-cyanophenyl)cyclohexyl]-1-propanal (121 g, 0.50 mol) obtained according to the method of Example 3 (i), in tetrahydrofuran (400 ml) at -10° C. over one hour, agitating the reaction mixture at 0° C. for one hour, further agitating at 20° C. for 2 hours, adding toluene (1 l) and water (1 l) to the reaction mixture at 0° C., four times washing the resulting toluene solution with water (1 l), drying over anhydrous magnesium sulfate, separating the drying agent, distilling off toluene, purifying the resulting residue according to silica gel column chromatography using heptane as an eluent to obtain trans-1-(4-methoxy-3-butenyl)-4-(4-cyanophenyl)cyclohexane (110.8 g, 0.41 mol), adding to the total quantity of this compound, tetrahydrofuran (1.5 l) and 2N-hydrochloric acid (0.4 l), heating the mixture under reflux, with stirring for one hour, cooling the resulting reaction mixture, adding diethyl ether (0.5 l) and water (1 l), three times washing the resulting diethyl ether solution with water (0.5 l), drying over anhydrous magnesium sulfate, separating the drying agent, concentrating under reduced pressure to obtain a residue (120 g), and recrystallizing from a mixed solvent of heptane and ethyl acetate (3:1) to obtain 4-[trans-4-(4-cyanophenyl)cyclohexyl]-1-butanal (93.0 g, 0.36 mol).

1. stirringagitating the reaction solution at 0° C. for one hour
2. customobtained
3. stirringagitating the reaction mixture at 0° C. for one hour
4. stirringfurther agitating at 20° C. for 2 hours
5. washfour times washing the resulting toluene solution with water (1 l)
6. dry with materialdrying over anhydrous magnesium sulfate
7. customseparating the drying agent
8. distillationdistilling off toluene
9. custompurifying the resulting residue