反应详情

温度

40 °C

A mixture of 2-acetoxy-1-(naphth-1-yl)-1-propanone (2.6 g), IMS (30 ml) and hydrochloric acid (1M; 22 ml) was boiled under reflux for 4 hours. The mixture was cooled, added to brine and extracted twice with dichloromethane. The combined organic extracts were dried with sodium sulphate, filtered and evaporated in vacuo to afford a mixture of crude 2-hydroxy-1-naphthalen-1-yl-propan-1-one and 1-hydroxy-1-naphthalen-1-yl-propan-1-one (B) as an oil (2.2 g). A portion of this material (0.5 g) was dissolved in tetrahydrofuran (2 ml) to which was added cyanamide (0.11 g), water (2 ml) and sodium hydroxide solution (2M; 0.25 ml). The mixture was stirred vigorously for 16 hours then tetrahydrofuran was added (10 ml). The mixture was heated to 40° C. for 30 minutes, cooled and left for a further 6 hours. Brine was added and the mixture was extracted twice with dichloromethane. The combined organic extracts were dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (3) (0.13 g; m.p. 187-189° C.) was obtained following silica gel column chromatography of the residue in 50% ethyl acetate in petroleum ether.

1. temperatureunder reflux for 4 hours
2. temperatureThe mixture was cooled
3. extractionextracted twice with dichloromethane
4. dry with materialThe combined organic extracts were dried with sodium sulphate
5. filtrationfiltered
6. customevaporated in vacuo
7. customto afford
8. temperaturecooled
9. waitleft for a further 6 hours
10. extractionthe mixture was extracted twice with dichloromethane
11. dry with materialThe combined organic extracts were dried with sodium sulphate
12. filtrationfiltered
13. customevaporated in vacuo