Water → HCID 178495003, 화합물

온도

-10 °C

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

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

ORD 기록

ord-6b18e6b43d5744a8adedac6542d9fa98

출처 데이터셋

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05053162