Alternatived Products of [ 1396893-45-0 ]
Product Details of [ 1396893-45-0 ]
| CAS No. : | 1396893-45-0 |
MDL No. : | MFCD28130321 |
| Formula : |
C12H17NO2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | YWHGVXSCPXKKFU-UHFFFAOYSA-N |
| M.W : |
207.27
|
Pubchem ID : | 121003044 |
| Synonyms : |
|
Safety of [ 1396893-45-0 ]
Application In Synthesis of [ 1396893-45-0 ]
* 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.
- Upstream synthesis route of [ 1396893-45-0 ]
- Downstream synthetic route of [ 1396893-45-0 ]
- 1
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[ 108-47-4 ]
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[ 105-58-8 ]
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[ 74-88-4 ]
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[ 1396893-45-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 2,4-lutidine With n-butyllithium In 2-methyltetrahydrofuran at -40 - -30℃; for 1.5h;
Stage #2: Diethyl carbonate In 2-methyltetrahydrofuran at -30 - 20℃; for 6h;
Stage #3: methyl iodide In 2-methyltetrahydrofuran at 0 - 25℃; for 1.66667h; |
5
To a solution of w-butyllithium (2.04 equiv.) in 2-methyltetrahydrofuran at maximum -40 °C was added a solution of 2,4-dimethylpyridine (e) (2.02 equiv.) in 2- methyltetrahydrofuran over 60 min, keeping the temperature below -30 °C. The reaction mixture was stirred for 30 min at maximum -30 °C. A solution of diethyl carbonate (1.00 equiv.) in 2-methyltetrahydrofuran was added over 60 min, keeping the temperature below -30 °C. The reaction was warmed to room temperature, and then stirred at this temperature for 5 h. After cooling to 0 °C, methyl iodide (2.15 equiv.) was charged over 40 min, keeping the temperature below 25 °C. The reaction was further stirred at room temperature for 1 h, then 1 M HC1 was added, and the pH was adjusted to a value of pH 8-9. After stirring for 15 min, the phases were separated, and the organic phase was washed with water. Distillation at 35 °C under vacuum then provided crude dimethylated ester (f ). Ester (f ) was subsequently added to a solution of sodium hydroxide (1.05 equiv.) in ethanol at 78 °C over 2 h. More ethanol was added, and the reaction was stirred at 78 °C for 10 h. The volume was reduced to approximately 50% by distillation under normal pressure. After cooling to room temperature, fert-butyl methyl ether was added, and the reaction mixture was stirred at this temperature for 30 min. Filtration was performed after cooling to 5-10 °C, and the filter cake was washed with dichloromethane. The wet product was dried at 60-70 °C under vacuum to give sodium carboxylate (g'). Compound (g') was reacted with sulfur tetrafluoride and hydrofluoric acid to afford compound (1). |
- 2
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[ 1396893-45-0 ]
-
[ 1217486-61-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: sodium hydroxide / ethanol / 12 h / 78 °C
2.1: hydrogen fluoride; sulfur tetrafluoride
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 °C
3.2: 1.5 h / -15 °C
3.3: 0.42 h / 10 - 20 °C / pH 2 - 4
4.1: N-Bromosuccinimide / toluene; ethanol / 1.5 h / 40 °C
5.1: pyridine / tetrahydrofuran / 1.5 h / 40 °C
6.1: water; tetrahydrofuran / 2.5 h / 60 °C |
|
- 3
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[ 1396893-45-0 ]
-
[ 1378865-93-0 ]
| Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol / 12 h / 78 °C
2: hydrogen fluoride; sulfur tetrafluoride |
|
- 4
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[ 1396893-45-0 ]
-
[ 1396893-39-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: sodium hydroxide / ethanol / 12 h / 78 °C
2.1: hydrogen fluoride; sulfur tetrafluoride
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 °C
3.2: 1.5 h / -15 °C
3.3: 0.42 h / 10 - 20 °C / pH 2 - 4 |
|
- 5
-
[ 1396893-45-0 ]
-
(x)BrH*C13H14F3N3S
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: sodium hydroxide / ethanol / 12 h / 78 °C
2.1: hydrogen fluoride; sulfur tetrafluoride
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 °C
3.2: 1.5 h / -15 °C
3.3: 0.42 h / 10 - 20 °C / pH 2 - 4
4.1: N-Bromosuccinimide / toluene; ethanol / 1.5 h / 40 °C |
|
- 6
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[ 1396893-45-0 ]
-
[ 1396893-46-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydroxide In ethanol at 78℃; for 12h; |
5
To a solution of w-butyllithium (2.04 equiv.) in 2-methyltetrahydrofuran at maximum -40 °C was added a solution of 2,4-dimethylpyridine (e) (2.02 equiv.) in 2- methyltetrahydrofuran over 60 min, keeping the temperature below -30 °C. The reaction mixture was stirred for 30 min at maximum -30 °C. A solution of diethyl carbonate (1.00 equiv.) in 2-methyltetrahydrofuran was added over 60 min, keeping the temperature below -30 °C. The reaction was warmed to room temperature, and then stirred at this temperature for 5 h. After cooling to 0 °C, methyl iodide (2.15 equiv.) was charged over 40 min, keeping the temperature below 25 °C. The reaction was further stirred at room temperature for 1 h, then 1 M HC1 was added, and the pH was adjusted to a value of pH 8-9. After stirring for 15 min, the phases were separated, and the organic phase was washed with water. Distillation at 35 °C under vacuum then provided crude dimethylated ester (f ). Ester (f ) was subsequently added to a solution of sodium hydroxide (1.05 equiv.) in ethanol at 78 °C over 2 h. More ethanol was added, and the reaction was stirred at 78 °C for 10 h. The volume was reduced to approximately 50% by distillation under normal pressure. After cooling to room temperature, fert-butyl methyl ether was added, and the reaction mixture was stirred at this temperature for 30 min. Filtration was performed after cooling to 5-10 °C, and the filter cake was washed with dichloromethane. The wet product was dried at 60-70 °C under vacuum to give sodium carboxylate (g'). Compound (g') was reacted with sulfur tetrafluoride and hydrofluoric acid to afford compound (1). |
- 7
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[ 1396893-45-0 ]
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[ 1396893-41-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: sodium hydroxide / ethanol / 12 h / 78 °C
2.1: hydrogen fluoride; sulfur tetrafluoride
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 °C
3.2: 1.5 h / -15 °C
3.3: 0.42 h / 10 - 20 °C / pH 2 - 4
4.1: N-Bromosuccinimide / toluene; ethanol / 1.5 h / 40 °C
5.1: pyridine / tetrahydrofuran / 1.5 h / 40 °C |
|
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