反応 #61839
ord-0a8fbca072a041dca7231b7ad252d79e
反応方程式
反応物
試薬
反応条件
後処理
- 1温度under reflux for 4 hours
- 2温度The mixture was cooled
- 3その他evaporated in vacuo
- 4その他partitioned between dichloromethane and brine
- 5その他The organic layer was separated
- 6乾燥dried with sodium sulphate
- 7ろ過filtered
- 8その他evaporated in vacuo
- 9その他to afford
- 10温度under reflux for 96 hours
- 11温度After cooling the volatiles
- 12その他were removed in vacuo
- 13温度The mixture was cooled
- 14その他triturated with chloroform (80 ml)
- 15ろ過filtered
- 16洗浄The filtrate was washed with water
- 17乾燥dried with sodium sulphate
- 18ろ過filtered
- 19その他evaporated in vacuo
実験手順
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.