Chloride → HCID 178495003, 화합물

온도

-10 °C

Commercially available methoxymethyltriphenylphosphornium chloride (15.7 g, 0.0458 mol) was added to tetrahydrofuran (100 ml), followed by dropwise adding a toluene solution (23 ml) of 25% by weight of phenyllithium in argon atmosphere with stirring at -10° C. over 10 minutes, agitating the reaction solution at 0° C. for 30 minutes, dropwise adding a solution of trans-4-(4-cyanophenyl)cyclohexylacetaldehyde (VII) obtained in Example 2(i) (7.3 g, 0.032 mol) in tetrahydrofuran (90 ml) at -10° C. over 10 minutes, agitating the reaction solution at 0° C. for 2 hours, adding toluene (100 ml) and water (200 ml), washing, subjecting the resulting toluene solution to three times washing with water (200 ml) and separating, drying with anhydrous sodium sulfate, separating the drying agent, distilling off toluene, dissolving the resulting residue in ethyl acetate (20 ml) on heating, allowing the solution to stand still at room temperature for one day, filtering off deposited crystals, concentrating the resulting mother liquor, dissolving the concentrate in heptane and purifying according to silica gel chromatography to obtain trans-1-(3-methoxy-2-propenyl)-4-(4-cyanophenyl)cyclohexane (4.4 g, 0.017 mol), adding to the total quantity thereof, tetrahydrofuran (70 ml) and 2N-hydrochloric acid (18 ml), heating the mixture under reflux with stirring for one hour, cooling the reaction solution, adding diethyl ether (50 ml) and water (50 ml) to the solution, subjecting the resulting diethyl ether to three times washing with water (50 ml) and separating, drying with anhydrous sodium sulfate, separating the drying agent and distilling off diethyl ether to obtain trans-4-(4-cyanophenyl)cyclohexylpropylaldehyde (4.2 g, 0.017 mol).

1. stirringagitating the reaction solution at 0° C. for 30 minutes
2. stirringagitating the reaction solution at 0° C. for 2 hours
3. washwashing
4. washwashing with water (200 ml)
5. customseparating
6. dry with materialdrying with anhydrous sodium sulfate
7. customseparating the drying agent
8. distillationdistilling off toluene
9. dissolutiondissolving the resulting residue in ethyl acetate (20 ml)
10. temperatureon heating
11. waitto stand still at room temperature for one day
12. filtrationfiltering off
13. concentrationconcentrating the resulting mother liquor
14. dissolutiondissolving the
15. concentrationconcentrate in heptane
16. custompurifying

ORD 기록

ord-c594a38a22994c71ad01e91fe4c5fda4

출처 데이터셋

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04880562