反应详情

To 0.85 g. sodium hydride in 150 ml. of dry dimethylformamide was added, portionwise, 9 g. of benzyl 1,2,3,4-tetrahydrocarbazole-4-carboxylate. The mixture was heated on a steam bath for 15 minutes, the heat was removed, 4 ml. benzoyl chloride was added dropwise to the still hot mixture and heating was resumed for two hours. The mixture, after standing overnight at room temperature, was poured into water containing 4 ml. glacial acetic acid and the resulting mixture was extracted with ether. The ether extract was washed with sodium bicarbonate solution and water, dried, and evaporated to dryness. The resulting residue in 50 ml. dimethylformamide was again treated with 0.42 g. sodium hydride and 2 ml. benzoyl chloride and worked up as described above and the resulting crude product was chromatographed on a 45 mm. by 620 mm. silica gel column using as eluant hexane and hexane containing increasing amounts of ether. There was thus obtained with 7.5% ether in hexane, after evaporation to dryness and recrystallization, 4.6 g. of the title compound; m.p. 107°-109°C. (methyl alcohol).

1. temperatureThe mixture was heated on a steam bath for 15 minutes
2. customthe heat was removed
3. additionbenzoyl chloride was added dropwise to the still hot mixture
4. temperatureheating
5. waitThe mixture, after standing overnight at room temperature
6. additionwas poured into water containing 4 ml
7. extractionglacial acetic acid and the resulting mixture was extracted with ether
8. extractionThe ether extract
9. washwas washed with sodium bicarbonate solution and water
10. customdried
11. customevaporated to dryness
12. additiondimethylformamide was again treated with 0.42 g
13. customwas chromatographed on a 45 mm
14. temperatureincreasing amounts of ether
15. customThere was thus obtained with 7.5% ether in hexane
16. customafter evaporation
17. customto dryness and recrystallization, 4.6 g