反应详情

温度

110 °C

To a solution of the Grignard reagent prepared from 0.71 g. (31 mmol) of magnesium and 5.3 g. (31 mmol) of 4-bromotoluene in 20 ml. of anhydrous tetrahydrofuran was added under an atmosphere of nitrogen a solution of 0.98 g. (6.0 mmol) of 5-cyano-1-methylpyrrole-2-acetic acid in 5 ml. of tetrahydrofuran. After the resulting yellow suspension was heated to the boiling point, 20 g. of diphenyl ether was added, and tetrahydrofuran was distilled from the reaction mixture until the temperature reached 110° C. The reaction mixture was then heated under reflux (110° C.) for 1.5 hours. During this time, the color of the suspension changed from yellow to dark orange. The reaction mixture was cooled and partitioned between ether and dilute aqueous hydrochloric acid. The ether phase was extracted with five percent aqueous sodium hydroxide solution, which was then acidified and extracted with methylene chloride. The methylene chloride solution was dried over magnesium sulfate and concentrated to give 30 mg. of purple liquid which contained only a trace of starting cyanoacid by nmr analysis. The aqueous phase was heated in a steam bath for four hours, and the resulting suspension was cooled and extracted with methylene chloride. The methylene chloride solution was dried over magnesium sulfate and concentrated to give 1.33 g. (86% yield) of 1-methyl-5-p-toluoyl-pyrrole-2-acetic acid as a brown solid.

1. temperatureAfter the resulting yellow suspension was heated to the boiling point, 20 g
2. distillationtetrahydrofuran was distilled from the reaction mixture until the temperature
3. customreached 110° C
4. temperatureThe reaction mixture was then heated
5. temperatureThe reaction mixture was cooled
6. custompartitioned between ether and dilute aqueous hydrochloric acid
7. extractionThe ether phase was extracted with five percent aqueous sodium hydroxide solution, which
8. extractionextracted with methylene chloride
9. dry with materialThe methylene chloride solution was dried over magnesium sulfate
10. concentrationconcentrated
11. customto give 30 mg
12. temperatureThe aqueous phase was heated in a steam bath for four hours
13. temperaturethe resulting suspension was cooled
14. extractionextracted with methylene chloride
15. dry with materialThe methylene chloride solution was dried over magnesium sulfate
16. concentrationconcentrated
17. customto give 1.33 g