反应详情

温度

115 °C

A mixture of 2-acetoxy-3-methyl-1-(naphth-1-yl)butan-1-one (8.4 g), IMS (200 ml) and hydrochloric acid (1M; 100 ml) were boiled under reflux for 4 hours. The mixture was cooled, evaporated in vacuo and partitioned between dichloromethane and brine. The organic layer was separated, dried with sodium sulphate, filtered and evaporated in vacuo to afford a mixture of crude 2-hydroxy-3-methyl-1-naphthalen-1-yl-butan-1-one and 1-hydroxy-3-methyl-1-naphthalen-1-yl-butan-2-one (F) (7.4 g). Cyanamide (1.3 g) and anhydrous ethanol (50 ml) were added and the resulting mixture was boiled under reflux for 96 hours. After cooling the volatiles were removed in vacuo and the residue heated at 115° C. for a further 48 hours. The mixture was cooled, triturated with chloroform (80 ml) and filtered. The filtrate was washed with water, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (7) was obtained (0.26 g; m.p. 127-129° C.) following silica gel column chromatography of the residue in 33% ethyl acetate in petroleum ether and re-crystallisation from dichloromethane/petroleum ether.

1. temperatureunder reflux for 4 hours
2. temperatureThe mixture was cooled
3. customevaporated in vacuo
4. custompartitioned between dichloromethane and brine
5. customThe organic layer was separated
6. dry with materialdried with sodium sulphate
7. filtrationfiltered
8. customevaporated in vacuo
9. customto afford
10. temperatureunder reflux for 96 hours
11. temperatureAfter cooling the volatiles
12. customwere removed in vacuo
13. temperatureThe mixture was cooled
14. customtriturated with chloroform (80 ml)
15. filtrationfiltered
16. washThe filtrate was washed with water
17. dry with materialdried with sodium sulphate
18. filtrationfiltered
19. customevaporated in vacuo