Alternatived Products of [ 191731-32-5 ]
Product Details of [ 191731-32-5 ]
| CAS No. : | 191731-32-5 |
MDL No. : | |
| Formula : |
C12H17NO4
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
239.27
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 191731-32-5 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 191731-32-5 ]
* 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 [ 191731-32-5 ]
- 1
-
[ 67442-07-3 ]
-
[ 105-13-5 ]
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2-(4-Methoxy-benzyloxy)-N-methyl-acetamide
[ No CAS ]
-
[ 191731-32-5 ]
- 2
-
[ 88920-24-5 ]
-
[ 6638-79-5 ]
-
[ 191731-32-5 ]
- 3
-
[ 67442-07-3 ]
-
[ 105-13-5 ]
-
[ 191731-32-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 9.85% |
In tetrahydrofuran; ethyl acetate; |
Step 1. N-methoxy-2-((4-methoxybenzyl)oxy)-N-methylacetamide To a suspension of sodium hydride (1.86 g, 46.5 mmol) in THF (80 ml) at 0° C. was added (4-methoxyphenyl)methyl alcohol (5.80 mL, 46.7 mmol) over 5 min. The reaction mixture was warmed to RT for 1 h, then cooled to 0° C. and a solution of <strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (6.50 g, 47.3 mmol) in THF (20 mL) was added. The reaction mixture was warmed to room temperature and stirred for 72 hr then quenched with NH4Cl and diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (2*) and the combined organic extracts were washed with brine (1*), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (120 g, 30percent to 80percent EtOAc in hexanes) gave N-methoxy-2-((4-methoxybenzyl)oxy)-N-methylacetamide (1.10 g, 4.60 mmol, 9.85percent yield) as a yellow oil. ESI (M+Na) 262.1. |
- 4
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[ 116272-41-4 ]
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[ 191731-32-5 ]
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[ 1600512-79-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 76% |
With n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate; |
Step 2. 1-(5-bromo-2-fluorophenyl)-2-((4-methoxybenzyl)oxy)ethanone To a solution of <strong>[116272-41-4]<strong>[116272-41-4]4-bromo-1-fluoro-2-iodobenze</strong>ne</strong> (1.85 g, 6.15 mmol) in THF (12 mL) at -78 C. was added dropwise butyllithium solution, 1.6m in hexane (3.85 ml, 6.16 mmol). The solution was stirred at -78 C. for 30 min and a solution of N-methoxy-2-((4-methoxybenzyl)oxy)-N-methylacetamide (1.10 g, 4.60 mmol) in THF (10 mL) at -78 C. was added via cannula. The reaction mixture was warmed from -78 C. to -10 C. over 1.5 h and quenched with NH4Cl and diluted with EtOAc and water. The aqueous phase was discarded and the organic phase was washed with brine (1*), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (40 g, 5% to 10% EtOAc in hexanes) gave 1-(5-bromo-2-fluorophenyl)-2-((4-methoxybenzyl)oxy)ethanone (1.24 g, 3.51 mmol, 76% yield) as a white solid. ESI (M+Na) 377.7. |
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