Methoxymethyl-triphenylphosphonium chloride → HCID 86746529, compound

Temperature

-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 toluene solution (23 ml) of phenyllithium in argon atmosphere with stirring at -10° C. over 10 minutes, agitating the reaction mixture at 0° C. for 30 minutes, dropwise adding a tetrahydrofuran solution (90 ml) of trans-4-(4-cyanophenyl)cyclohexylacetaldehyde (7.3 g, 0.032 mol) obtained in Example 2 (i) at -10° C. over 10 minutes, agitating the reaction mixture at 0° C. for 2 hours, washing by adding toluene (100 ml) and water (200 ml), further three times washing the 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 at room temperature for one day, filtering off deposited crystals, concentrating the mother liquor, dissolving the concentrate in heptane, purifying by 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, tetrahydrofuran (70 ml) and 2N-hydrochloric acid (18 ml), heating the mixture for 1h. under reflux with stirring, cooling the reaction mixture, adding diethyl ether (50 ml) and water (50 ml), three times washing the resulting diethyl ether solution with water (50 ml), drying it 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. washwashing
4. additionby adding toluene (100 ml) and water (200 ml), further three times
5. washwashing the toluene solution with water (200 ml)
6. dry with materialdrying over anhydrous sodium sulfate
7. customseparating the drying agent
8. distillationdistilling off toluene
9. dissolutiondissolving the residue in ethyl acetate (20 ml)
10. temperatureon heating
11. waitto stand at room temperature for one day
12. filtrationfiltering off
13. concentrationconcentrating the mother liquor
14. dissolutiondissolving the
15. concentrationconcentrate in heptane
16. custompurifying by silica gel column chromatography

ORD record

ord-a64dfcf130a54c3f9342f92ee053a391

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05183587