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Chemical Structure| 18596-80-0 Chemical Structure| 18596-80-0

Structure of 18596-80-0

Chemical Structure| 18596-80-0

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Product Details of [ 18596-80-0 ]

CAS No. :18596-80-0
Formula : C5H9NO2
M.W : 115.13
SMILES Code : COC1=NCCOC1
MDL No. :MFCD18633123

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Application In Synthesis of [ 18596-80-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 18596-80-0 ]

[ 18596-80-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 109-11-5 ]
  • [ 77-78-1 ]
  • [ 18596-80-0 ]
YieldReaction ConditionsOperation in experiment
Example 1 3-Morpholinone (10.1 g) was dissolved in toluene (100 ml) and the solution was heated to 70 C. To the resulting solution dimethyl sulphate (12.6 q) was added dropwise over a period of 30 minutes.. After the completion of this addition, the reaction mixture was heated under reflux for 6 hours.. After having been allowed to cool, the reaction mixture was admixed portionwise with anhydrous potassium carbonate (13.8 g), while being kept in an ice bath. After one hour stirring, the separated salt was filtered off and the filtrate was concentrated to obtain crude 3-methoxy-5,6-dihydro-2H-oxazine (8 g)..
  • 2
  • [ 109-11-5 ]
  • [ 420-37-1 ]
  • [ 18596-80-0 ]
YieldReaction ConditionsOperation in experiment
44% In dichloromethane; at 20℃; To a solution of <strong>[109-11-5]3-morpholone</strong> (2.0 g, 20 mmol) in dichloromethane (40 mL) in a 100 mL single neck flask was added trimethyloxonium tetrafluoroborate (4.0 g, 27 mmol), the mixture was stirred at room temperature overnight. The mixture was quenched with saturated aqueous sodium bicarbonate solution (50 mL) under ice bath, and then adjusted pH to neutral. The mixture was extracted with dichloromethane (50 mL x 2). The combined organic layers were washed with saturated brine (50 mL x 2), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give the title compound as a transparent oil (1.0 g, 44%).‘H NIVIR (400 1VIFIz5 CDC13) 4.01 (d, J 1.2 H4 2H’), 3.65 (d, J 2.3 H4 3H), 3.62 (dd, J 6.5, 3.2 Hz; 2H’), 3.51 (dd, J 6.5, 2.9 Hz, 2H).
Example 9A5 -Methoxy-3 ,6-dihydro-2H- 1 ,4-oxazineA solution of 1.2 g (11.9 mmol) <strong>[109-11-5]morpholine-3-one</strong> in dichloromethane (70 ml) was cooled to 00C and treated with 25 g (238 mmol) dry sodium carbonate. After stirring for 10 min at 00C, 6.14 g (41.5 mmol) trimethyloxonium tetrafluoroborate were added at 00C. The mixture was allowed to warm to room temperature and stirred for 6 h. Water (100 ml) was added, and the organic layer was separated. The aqueous phase was extracted several times with dichloromethane, and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was used in the next step without further purification.GC-MS (method 3): R1 = 3.36 min; MS (ESIpos): m/z = 116 (M+H)+.
A solution of 1.2 g (1 1.9 mmol) <strong>[109-11-5]morpholine-3-one</strong> in dichloromethane (70 ml) was cooled to 0C and treated with 25 g (238 mmol) dry sodium carbonate. After stirring for 10 min at 0C, 6.14 g (41.5 mmol) trimethyloxonium tetrafluorob orate were added at 0C. The mixture was allowed to warm to room temperature and stirred for 6 h. Water (100 ml) was added, and the organic layer was separated. The aqueous phase was extracted several times with dichloromethane, and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was used in the next step without further purification.GC-MS (method 5): Rt = 3.36 min; MS (ESIpos): m/z = 1 16 (M+H)+.
Example 3A5-Methoxy-3,6-dihydro-2H-l ,4-oxazine A solution of 1.2 g (11.9 mmol) <strong>[109-11-5]morpholine-3-one</strong> in dichloromethane (70 ml) was cooled to 00C and treated with 25 g (238 mmol) dry sodium carbonate. After stirring for 10 min at 0C, 6.14 g (41.5 mmol) trimethyloxonium tetrafluoroborate were added at 0C. The mixture was allowed to warm to room temperature and stirred for 6 h. Water (100 ml) was added, and the organic layer was separated. The aqueous phase was extracted several times with dichloromethane, and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was used in the next step without further purification.GC-MS (method 3): R, = 3.36 min; MS (ESIpos): m/z = 116 (M+?)+.

 

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