반응 #59985
ord-da0e9ed2068443b396feb9605a9e8a38
반응 방정식
반응 조건
후처리
- 1기타separator was attached to a round bottom flask
- 2온도The mixture was heated
- 3온도under reflux for 3 hours
- 4농축the mixture was concentrated
- 5건조After dried over sodium sulfate
- 6여과the mixture was filtrated
- 7농축The filtrate was concentrated under reduced pressure
- 8기타purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/2, 1/1, 2/1)
실험 절차
A reflux condenser equipped with a Dean-Stark water separator was attached to a round bottom flask containing ethyl 4-cyclohexanonecarboxylate (5 ml, 31.4 mmol), ethylene glycol (1.93 ml, 34.5 mmol), p-toluenesulfonic acid monohydrate (200 mg, 1.05 mmol), and benzene (30 ml). The mixture was heated under reflux for 3 hours. To the reaction mixture, triethylamine (181 μl, 1.3 mmol) was added and the mixture was concentrated. A tetrahydrofuran solution of the resultant crude substance was added to a tetrahydrofuran (30 ml) suspension of lithium aluminum hydride (1.31 g, 34.5 mmol) at 0° C. After the mixture was stirred at room temperature for 7 hours, water (1.3 ml), a 5N aqueous sodium hydroxide solution (1.3 ml), and water (3.9 ml) were sequentially added to the mixture at 0° C. After dried over sodium sulfate, the mixture was filtrated. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/2, 1/1, 2/1) to obtain the title compound (4.6 g, yield: 85.1%) as a colorless oil.