Methoxymethyl-triphenylphosphonium chloride → HCID 178494950, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available methoxymethyltriphenylphosphonium chloride (120.8 g, 0.35 mol) was added to tetrahydrofuran (400 ml), followed by adding potassium t-butoxide (39.5 g, 0.35 mol) in argon atmosphere with stirring at -10° C. over 20 minutes, agitating the reaction mixture at 0° C. for one hour, dropwise adding a solution of 4-[trans-4-(4-cyanophenyl)cyclohexyl]-1-butanal (60.0 g, 0.23 mol) obtained according to the method of Example 4 (i), in tetrahydrofuran (300 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., 4 times washing the resulting toluene solution with water (1 l), drying over anhydrous magnesium sulfate, separating the drying agent, distilling off toluene, purifying the residue according to silica gel column chromatography using heptane as an eluent to obtain trans-1-(5-methoxy-4-pentenyl)-4-(4-cyanophenyl)cyclohexane (52.6 g, 0.19 mol), adding to the total quantity of this compound, tetrahydrofuran (750 ml) and 2N-hydrochloric acid (190 ml), heating the mixture under reflux with stirring for one hour, cooling the resulting solution, adding diethyl ether (0.5 l) and water (1 l) to the reaction mixture, 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, recrystallizing the resulting residue (50 g) from a mixed solvent of heptane and ethyl acetate (3:1), and drying to obtain 5-[trans-4-(4-cyanophenyl)cyclohexyl]-1-pentanal (43.1 g, 0.16 mol).

Provenance & Evidence