تفاعل #2545
ord-b9a7125374424a33a8c178a8e25b8efd
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةheated
- 2درجة الحرارةunder reflux for 4 hours
- 3تركيزAfter concentrating the reaction solution to 1/3 volume, insoluble materials
- 4أخرىwere removed by filtration
- 5درجة الحرارةTo the resulting filtrate cooled in an ice bath
- 6أخرىThe resulting reaction mixture
- 7استخلاصextracted with methylene chloride
- 8غسيلwashed with 10% citric acid aqueous solution, water and saturated brine in that order
- 9تجفيفAfter drying on anhydrous magnesium sulfate
- 10أخرىremoving the solvent
- 11أخرىby evaporation
- 12أخرىto obtain creamy-colored powder
- 13workup.ADDITIONTo this were added
- 14درجة الحرارةof heating
- 15درجة الحرارةunder reflux
- 16ترشيحfiltering off the formed insoluble materials
- 17أخرىthe organic solvent was removed by evaporation
- 18استخلاصThe resulting residue was extracted with ethyl acetate
- 19غسيلthe organic layer was washed with saturated brine
- 20تجفيفdried on anhydrous magnesium sulfate
- 21أخرىfollowed by the removal of the solvent by evaporation
- 22أخرىto obtain an orange oily material
- 23workup.STIRRINGAfter 1 hour of stirring at the same temperature
- 24درجة الحرارةwarmed to room temperature
- 25أخرىAfter removing methanol
- 26أخرىby evaporation, ethyl acetate extraction
- 27غسيلthe resulting organic layer was washed with saturated brine
- 28تجفيفdried on anhydrous magnesium sulfate
- 29أخرىsubjected to evaporation
- 30أخرىto remove the solvent
- 31غسيلthe resulting colorless solid material was washed with an ether-hexane (2:1) mixture solution
الإجراء التجريبي
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.