Technology Process of [(2R,3S,3aR)-3a-Allyl-3-methyl-2-(3,4,5-trimethoxy-phenyl)-2,3,3a,4-tetrahydro-benzofuran-6-yloxy]-trimethyl-silane
There total 12 articles about [(2R,3S,3aR)-3a-Allyl-3-methyl-2-(3,4,5-trimethoxy-phenyl)-2,3,3a,4-tetrahydro-benzofuran-6-yloxy]-trimethyl-silane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 90 percent / TiCl4, pyridine / Ambient temperature
2: concentrated HCl / methanol / Heating
3: NaBH4 / methanol / 5 °C
4: 92 percent / triethylamine / methanol / 5 °C
5: 1.) alkaline hydrolysis, methanol, reflux; 2.) decarboxylation
6: 87 percent / BF3*Et2O, tetramethyl orthocarbonate / CH2Cl2 / Ambient temperature
7: 76 percent / lithium diisopropylamide / tetrahydrofuran
8: 68 percent / dilute HCl / methanol
9: 1.) potassium t-butoxide; 2.) p-toluenesulfonic acid / 1.) THF, reflu; 2.) benzene, reflux
10: lithium diisopropylamide / 1,2-dimethoxy-ethane
With
pyridine; hydrogenchloride; sodium tetrahydroborate; tetramethoxymethane; boron trifluoride diethyl etherate; potassium tert-butylate; titanium tetrachloride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1246/cl.1984.67
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 84 percent / butyllithium / tetrahydrofuran / Ambient temperature
2: pyridine
3: N-chlorosuccinimide, aqueous aceton / 10 - 16 °C
4: 90 percent / TiCl4, pyridine / Ambient temperature
5: concentrated HCl / methanol / Heating
6: NaBH4 / methanol / 5 °C
7: 92 percent / triethylamine / methanol / 5 °C
8: 1.) alkaline hydrolysis, methanol, reflux; 2.) decarboxylation
9: 87 percent / BF3*Et2O, tetramethyl orthocarbonate / CH2Cl2 / Ambient temperature
10: 76 percent / lithium diisopropylamide / tetrahydrofuran
11: 68 percent / dilute HCl / methanol
12: 1.) potassium t-butoxide; 2.) p-toluenesulfonic acid / 1.) THF, reflu; 2.) benzene, reflux
13: lithium diisopropylamide / 1,2-dimethoxy-ethane
With
pyridine; hydrogenchloride; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; tetramethoxymethane; boron trifluoride diethyl etherate; potassium tert-butylate; titanium tetrachloride; toluene-4-sulfonic acid; triethylamine; acetone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1246/cl.1984.67
- Guidance literature:
-
Multi-step reaction with 12 steps
1: pyridine
2: N-chlorosuccinimide, aqueous aceton / 10 - 16 °C
3: 90 percent / TiCl4, pyridine / Ambient temperature
4: concentrated HCl / methanol / Heating
5: NaBH4 / methanol / 5 °C
6: 92 percent / triethylamine / methanol / 5 °C
7: 1.) alkaline hydrolysis, methanol, reflux; 2.) decarboxylation
8: 87 percent / BF3*Et2O, tetramethyl orthocarbonate / CH2Cl2 / Ambient temperature
9: 76 percent / lithium diisopropylamide / tetrahydrofuran
10: 68 percent / dilute HCl / methanol
11: 1.) potassium t-butoxide; 2.) p-toluenesulfonic acid / 1.) THF, reflu; 2.) benzene, reflux
12: lithium diisopropylamide / 1,2-dimethoxy-ethane
With
pyridine; hydrogenchloride; sodium tetrahydroborate; N-chloro-succinimide; tetramethoxymethane; boron trifluoride diethyl etherate; potassium tert-butylate; titanium tetrachloride; toluene-4-sulfonic acid; triethylamine; acetone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1246/cl.1984.67
