Реакция #458735
ord-3f2fbf27a3a54242a775e795566bf64f
Уравнение реакции
Реактанты
Реагенты
Условия реакции
Обработка
- 1ТемператураThe mixture was warmed
- 2Температураto reflux for a few minutes
- 3workup.WAITAfter 3 days the indicator turned green
- 4ДругоеThe liquid was then removed by rotary evaporation
- 5Другоеto give a yellow solid
- 6Фильтрацияcollected by filtration
- 7ПромывкаThe resulting solid was washed with additional 20% HCl solution (250 mL)
- 8Другоеsucked dry
- 9ДругоеThe slightly yellow solid was then recrystallized from CH3OH/Et2O
Методика
To a 2 L Erlenmeyer flask was added 3-fluoranthenecarbaldehyde (11.51 g, 50 mmol) 2-methyl-2-amino-1,3-propanediol (Aldrich, 5.52 g, 52.5 mmol), p-toluenesulfonic acid.H2O (Eastman Kodak Co., Rochester, NY, 14650, 0.1 g, 0.5 mmol), and PhCH3 (500 mL). The mixture was warmed to reflux for a few minutes and H2O (2-3 mL) was driven off. The resulting golden colored solution was allowed to cool to RT, diluted with absolute EtOH (500 mL) and stirred overnight. NaBH3CN (Aldrich, 95%, 1.57 g, 25 mmol) was added to the reaction. After the NaBH3CN dissolved, an indicator (bromocresol green, Eastman, 5 mg) was added. To the resulting blue solution was added 5 drops of 1M solution of HCl gas in absolute EtOH every 15 minutes. After 3 days the indicator turned green then yellow and voluminous white precipitate was present in the flask. To the flask was then added 1M HCl gas (10 mL) in absolute EtOH, and H2O (10 mL). The liquid was then removed by rotary evaporation to give a yellow solid. The solid was shaken with 20% HCl solution (500 mL) and collected by filtration. The resulting solid was washed with additional 20% HCl solution (250 mL) and then with CH 2 Cl2 (4×250 mL), pressed and then sucked dry. The slightly yellow solid was then recrystallized from CH3OH/Et2O to give 11.80 g (66%) of 2-((3-fluoranthenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride mp 262°-265° (dec), (,H,Cl,N).