反应详情

温度

50 °C

A mixture of 2,4-dimethyl-1H-pyrrole (2.0 ml, 19.42 mmol) and 2-(pyrrolidin-1-ylsulfonyl)benzaldehyde (4.65 g, 19.42 mmol) in trifluoroethanol (48.6 ml) and 12.5 sodium hydroxide (1.554 ml, 19.42 mmol) was heated at 50° C. for 1 h. The mixture was poured into ice and the resulting murky solution was decanted. The remaining residue was taken up in benzene and concentrated under vacuum. This residue was diluted in DCM (48.6 ml) and cooled to 0° C. To this solution, were added TFA (7.48 ml, 97 mmol) and triethylsilane (31.0 ml, 194 mmol). This mixture was heated at reflux (50° C.) for 15 min and poured into a mixture of ice and saturated solution of sodium bicarbonate. The mixture was extracted with dichloromethane (100 ml×2). The organic layers were combined, washed with brine (50 ml), dried, filtered, and concentrated to give an oil. Purification of the oil by column chromatography (0 to 20% ethyl acetate in hexanes) gave 2,4-dimethyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole (380.0 mg, 1.193 mmol, 6.14% yield,) [Rf=0.73 (20% ethyl acetate in hexanes)] and 3,5-dimethyl-2-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole (1.07 g, 3.36 mmol, 17.30% yield) [Rf=0.63 (20% ethyl acetate in hexanes)].

1. additionThe mixture was poured into ice
2. customthe resulting murky solution was decanted
3. concentrationconcentrated under vacuum
4. additionThis residue was diluted in DCM (48.6 ml)
5. temperaturecooled to 0° C
6. temperatureThis mixture was heated
7. temperatureat reflux (50° C.) for 15 min
8. extractionThe mixture was extracted with dichloromethane (100 ml×2)
9. washwashed with brine (50 ml)
10. customdried
11. filtrationfiltered
12. concentrationconcentrated
13. customto give an oil
14. customPurification of the oil by column chromatography (0 to 20% ethyl acetate in hexanes)