Dichloromethane → HCID 67550055, compound

Participants

Reaction Steps

To a methylene chloride suspension of aluminum chloride, a methylene chloride solution of (R)-2-(3-methoxyphenyl)propionic acid chloride was added dropwise under ice cooling. After stirring at the same temperature for 15 minutes, a methylene chloride solution of trans-4-propylcyclohexylbenzene was added dropwise. After the completion of the reaction, the reaction system was added to iced water and the organic layer was separated by adding methylene chloride. The organic layer was washed twice with water and then washed with saturated brine. The aqueous layer was washed with methylene chloride and, after combining the organic layer, the solvent was concentrated to obtain a crude product of (R)-1-(4-cyclohexylphenyl)-2-(3-methoxyphenyl)-propan-1-one. To an ethylene glycol solution of the resulting crude product, hydrazine monohydrate was added and the solution was stirred at 110° C. while removing water as a by-product. After efflux of water has nearly terminated, excess hydrazine was distilled off by stirring at 120° C. The temperature of the reaction system was reduced and potassium hydroxide was added, followed by heating to 160° C. After the completion of the reaction, the temperature of the reaction system was reduced and water and toluene were added, followed by stirring. After separating the organic layer, the aqueous layer was washed with toluene and the organic layer was combined and then washed three times with water. The residue was washed with saturated brine and concentrated to obtain a crude product of a compound represented by the formula (XI-a). The resulting crude product was purified by column chromatography and recrystallized from ethanol to obtain (S)-1-{2-(3-methoxyphenyl)propyl}-4-(trans-4-propylcyclohexyl) benzene (S-isomer of the compound represented by the formula (XI-a)).

Provenance & Evidence