4,4'-Dimethoxybenzophenone → Tas-301

Participants

Reaction Steps

10.0 g of oxindole was dissolved in 100 ml tetrahydrofuran, and 21.8 g of 4,4'-dimethoxybenzophenone was added thereto at room temperature. Subsequently, the temperature of the reaction was brought to 0° C. 9.0 g of 60% sodium hydride was added, and when generation of hydrogen ceased, the reaction mixture was refluxed with heat for 12 hours. After completion of reaction, the reaction mixture was cooled. Saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over sodium sulfate, and then evaporated. The resultant crude product was recrystallized from methanol, to thereby obtain 22.8 g (yield 85%) of the title compound in yellow crystals (Crystal 1). The melting point and elementary analysis data are shown in Table 1, and NMR and MS spectrum data are shown in Table 2. Also, the IR spectrum chart of the compound is shown in FIG. 1.

Provenance & Evidence