反应详情

To a lithium bis(trimethylsilyl)amide (1M; tetrahydrofuran solution) (21 ml), a tetrahydrofuran (100 ml) solution of p-toluenesulfonylmethylisocyanide (4.04 g) was added dropwise at −78° C., and the mixture was stirred for 30 minutes. Successively, a tetrahydrofuran (20 ml) solution of dimethyl glutaconate (3.78 g) was added dropwise thereto, followed by stirring while raising the temperature to room temperature for 2 hours. The reaction mixture was concentrated, and the residue was washed with water and 1N hydrochloric acid successively, followed by extraction with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:2) to give the title compound (2.11 g) having the following physical properties.

1. stirringby stirring
2. concentrationThe reaction mixture was concentrated
3. washthe residue was washed with water and 1N hydrochloric acid successively
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic layer was washed with 1N hydrochloric acid
6. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water and brine successively, dried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:2)