4,4'-Dimethoxybenzophenone → 3-[1-Hydroxy-1,1-bis(4-methoxyphenyl)methyl]-N,N-diisopropyl-4-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

In 480 ml of dry tetrahydrofuran was dissolved 81.5 ml of diisopropylamine under nitrogen atmosphere, and the solution was cooled to -70° C. Then, 375 ml of 1.6N n-butyllithium was dropwise added to the extent that the temperature of the mixture was not higher than -65° C., to thereby produce lithium diisopropylamide. The reaction mixture was kept at -70° C. for one hour, and to the reaction mixture was added a solution of 43.97 g of N,N-diisopropylisonicotinamide in 150 ml of dry tetrahydrofuran, to the extent that the temperature of the mixture was not higher than -65° C. The mixture was stirred for one hour and 15 minutes, and to the reaction mixture was dropwise added a solution of 46.94 g of 4,4'-dimethoxybenzophenone in 945 ml of dry tetrahydrofuran to the extent that the temperature of the mixture was not higher than -65° C., followed by stirring for 15 minutes. Thereafter, the temperature was allowed to be brought back to room temperature, and water was added thereto. After extraction with ethyl acetate, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 63.69 g of the desired compound as a solid.

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