反应详情

温度

95 °C

Methyl 5-acetyl-2-methoxybenzoate (11.98 g, 48.0 mmol) was added to N,N-dimethylformamide dimethyl acetal (44.6 g, 374.5 mmol) held under a nitrogen atmosphere. The resulting solution was heated at 95° C. for 60 minutes. Methanol (10 ml) was then removed by atmospheric distillation and further N,N-dimethylformamide dimethyl acetal (8.90 g, 74.9 mmol) added. The resulting solution was heated at 95° C. for a further 270 minutes. The reaction was then cooled to 50° C. and ethyl acetate (35 mL) added. Solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (35 mL) added. Further solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (50 mL) added. The reaction mixture is cooled to RT whereby the desired product crystallises out as a granular, free flowing solid. The solid was isolated by filtration, washed twice with fresh ethyl acetate (2×30 mL) and dried to constant weight to afford 11.39 g of the desired methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoate (8).

1. additionadded
2. temperatureThe resulting solution was heated at 95° C. for a further 270 minutes
3. temperatureThe reaction was then cooled to 50° C.
4. customSolvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (35 mL)
5. additionadded
6. customFurther solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (50 mL)
7. additionadded
8. temperatureThe reaction mixture is cooled to RT whereby the desired product
9. customcrystallises out as a granular,
10. customThe solid was isolated by filtration
11. washwashed twice with fresh ethyl acetate (2×30 mL)
12. customdried to constant weight