Technology Process of ethyl-(4-(benzyloxy)-1-hydroxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate
There total 6 articles about ethyl-(4-(benzyloxy)-1-hydroxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
ethyl bromoacetate;
With
chloro-trimethyl-silane; zinc;
In
tetrahydrofuran;
at 20 - 45 ℃;
for 1.5h;
2-(benzyloxy)-4-(tetrahydro-2H-pyran-2-yloxy)-6-(3,3,4,4-tetramethylborolan-1-yl)benzaldehyde;
zinc;
In
tetrahydrofuran;
at -78 - 0 ℃;
for 0.5h;
Ice bath;
With
ammonium chloride;
In
tetrahydrofuran;
Product distribution / selectivity;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: trichlorophosphate / 1 h / 0 - 100 °C
2.1: boron tribromide / dichloromethane / -78 - 20 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
6.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 1.5 h / 20 - 45 °C
6.2: 0.5 h / -78 - 0 °C / Ice bath
With
chloro-trimethyl-silane; potassium acetate; boron tribromide; potassium carbonate; zinc; trichlorophosphate;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; pyridinium p-toluenesulfonate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: boron tribromide / dichloromethane / -78 - 20 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
5.1: chloro-trimethyl-silane; zinc / tetrahydrofuran / 1.5 h / 20 - 45 °C
5.2: 0.5 h / -78 - 0 °C / Ice bath
With
chloro-trimethyl-silane; potassium acetate; boron tribromide; potassium carbonate; zinc;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; pyridinium p-toluenesulfonate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
