反应详情

温度

110 °C

A mixture of 2-acetoxy-3-methyl-1-(4′-fluoronaphth-1-yl)butan-1-one (4.8 g), IMS (100 ml) and hydrochloric acid (1M; 70 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. The residue was purified by silica gel column chromatography in 66-100% dichloromethane in petroleum ether to afford a mixture of 2-hydroxy-3-methyl-1-(4′-fluoronaphth-1-yl)butan-1-one and 1-hydroxy-3-methyl-l-(4′-fluoronaphth-1-yl)butan-2-one (3.2 g). Cyanamide (0.65 g) and anhydrous ethanol (10 ml) were added and the resulting mixture was boiled under reflux for 48 hours. After cooling the volatiles were removed in vacuo and the residue heated at 110° C. for a further 48 hours. The mixture was cooled, triturated with chloroform (100 ml) and filtered. The filtrate was washed with water, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (0.25 g; m.p. 141° C., softens from 125° 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. 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. customThe residue was purified by silica gel column chromatography in 66-100% dichloromethane in petroleum ether
10. customto afford
11. temperatureunder reflux for 48 hours
12. temperatureAfter cooling the volatiles
13. customwere removed in vacuo
14. temperatureThe mixture was cooled
15. customtriturated with chloroform (100 ml)
16. filtrationfiltered
17. washThe filtrate was washed with water
18. dry with materialdried with sodium sulphate
19. filtrationfiltered
20. customevaporated in vacuo