反应详情

To a stirred mixture of 10.5 g of N-(2,3-dihydro- 1H-inden-5-yl)acetamide and 4.7 ml of acetyl chloride in 100 ml of carbondisulfide were added portionwise 17.3 g of aluminum chloride at room temperature. After stirring for 2 hours at reflux temperature, the cooled reaction mixture was poured into 50 ml ice/HCl. The separated aqueous layer was extracted with dichloromethane. The extract was combined with the former organic layer, washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; dichloromethane/methanol 99:1 ). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The crystallized product was filtered off and dried, yielding 6.3 g (48.3%) of N-(6-acetyl-2,3-dihydro- 1H-inden-5-yl)acetamide (interm. 1).

1. temperatureat reflux temperature
2. customthe cooled reaction mixture
3. extractionThe separated aqueous layer was extracted with dichloromethane
4. washwashed with water
5. customdried
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by column chromatography (silica gel; dichloromethane/methanol 99:1 )
9. customThe eluent of the desired fraction was evaporated
10. customthe residue was crystallized from 2,2'-oxybispropane
11. filtrationThe crystallized product was filtered off
12. customdried