반응 #2545
ord-b9a7125374424a33a8c178a8e25b8efd
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후처리
- 1온도heated
- 2온도under reflux for 4 hours
- 3농축After concentrating the reaction solution to 1/3 volume, insoluble materials
- 4기타were removed by filtration
- 5온도To the resulting filtrate cooled in an ice bath
- 6기타The resulting reaction mixture
- 7추출extracted with methylene chloride
- 8세척washed with 10% citric acid aqueous solution, water and saturated brine in that order
- 9건조After drying on anhydrous magnesium sulfate
- 10기타removing the solvent
- 11기타by evaporation
- 12기타to obtain creamy-colored powder
- 13workup.ADDITIONTo this were added
- 14온도of heating
- 15온도under reflux
- 16여과filtering off the formed insoluble materials
- 17기타the organic solvent was removed by evaporation
- 18추출The resulting residue was extracted with ethyl acetate
- 19세척the organic layer was washed with saturated brine
- 20건조dried on anhydrous magnesium sulfate
- 21기타followed by the removal of the solvent by evaporation
- 22기타to obtain an orange oily material
- 23workup.STIRRINGAfter 1 hour of stirring at the same temperature
- 24온도warmed to room temperature
- 25기타After removing methanol
- 26기타by evaporation, ethyl acetate extraction
- 27세척the resulting organic layer was washed with saturated brine
- 28건조dried on anhydrous magnesium sulfate
- 29기타subjected to evaporation
- 30기타to remove the solvent
- 31세척the resulting colorless solid material was washed with an ether-hexane (2:1) mixture solution
실험 절차
N-Bromosuccinimide (1.29 g, 7.2 mmol) and AIBN (50 mg, 0.30 mmol) were suspended in carbon tetrachloride (80 ml), mixed with m-toluyl chloride (0.8 ml, 6.0 mmol) and then heated under reflux for 4 hours while exposing to light. After concentrating the reaction solution to 1/3 volume, insoluble materials were removed by filtration. To the resulting filtrate cooled in an ice bath were added dropwise o-anisidine (0.69 ml, 6 mmol) and 20% sodium hydroxide aqueous solution (5 ml) in that order. The resulting reaction mixture was stirred for 20 minutes at room temperature, extracted with methylene chloride and then washed with 10% citric acid aqueous solution, water and saturated brine in that order. After drying on anhydrous magnesium sulfate and removing the solvent by evaporation, the resulting light beige solid material was subjected to silica gel column chromatography (ether:hexane=1:1) to obtain creamy-colored powder. To this were added precipitated calcium carbonate (2.34 g, 23.4 mmol) and a dioxane-water (1:1) mixture solution (20 ml), followed by 6 hours of heating under reflux. After adding THF (50 ml) and filtering off the formed insoluble materials, the organic solvent was removed by evaporation. The resulting residue was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate, followed by the removal of the solvent by evaporation to obtain an orange oily material. This was dissolved in methanol (15 ml), and sodium borohydride (90 mg, 2.34 mmol) was added to the solution in one portion at -15° C. After 1 hour of stirring at the same temperature, the reaction mixture was mixed with acetone (1 ml), warmed to room temperature and then mixed with saturated ammonium chloride aqueous solution (10 ml). After removing methanol by evaporation, ethyl acetate extraction was carried out, and the resulting organic layer was washed with saturated brine, dried on anhydrous magnesium sulfate and then subjected to evaporation to remove the solvent. The thus obtained residue was subjected to silica gel column chromatography (ether:hexane=3:1), and the resulting colorless solid material was washed with an ether-hexane (2:1) mixture solution to obtain 1.02 g (66.1%) of the title compound in the form of colorless powder.