(S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

Base Information

Chemical Name:(S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane
CAS No.:951161-65-2
Molecular Formula:C₂₃H₄₀O₃Si
Molecular Weight:392.654
Hs Code.:

Synonyms:(S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

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Chemical Property of (S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

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Technology Process of (S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

There total 7 articles about (S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 951161-59-4
(S)-2-[3-(2,3-dimethoxy-4-methyl-phenyl)-butyl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

: 951161-60-7
(E)-((3-bromo-2-methylallyl)oxy)(tert-butyl)dimethylsilane

: 951161-65-2
(S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

Guidance literature:: (S)-2-[3-(2,3-dimethoxy-4-methyl-phenyl)-butyl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - -10 ℃; for 3h;

With sodium acetate; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; cyclohexane; at -10 ℃;

(E)-((3-bromo-2-methylallyl)oxy)(tert-butyl)dimethylsilane; In tetrahydrofuran; cyclohexane; at 85 ℃; for 24h; Further stages.;
DOI:10.1021/ol071228v

Reference yield:

: 951161-56-1
2,3-dimethoxy-1-methyl-4-vinylbenzene

: 951161-65-2
(S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: chiral phosphite ligand; catecholborane / [Ph(COD)2]BF₄ / 1,2-dimethoxy-ethane / 2.5 h / -45 °C

1.2: 1,2-dimethoxy-ethane; tetrahydrofuran / -45 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -90 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / -90 - 20 °C

4.1: sec-BuLi / tetrahydrofuran; cyclohexane / 3 h / -78 - -10 °C

4.2: sodium acetate / [Pd(dppf)Cl₂]*CH₂Cl₂ / tetrahydrofuran; cyclohexane / -10 °C

4.3: tetrahydrofuran; cyclohexane / 24 h / 85 °C

With n-butyllithium; chiral phosphite ligand; sec.-butyllithium; benzo[1,3,2]dioxaborole; [Ph(COD)2]BF₄; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; cyclohexane;
DOI:10.1021/ol071228v

Reference yield:

: 91-16-7
1,2-dimethoxybenzene

: 951161-65-2
(S,E)-tert-butyl-[6-(2,3-dimethoxy-4-methyl-phenyl)-2-methyl-hept-2-enyloxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 3.5 h / 20 °C

1.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: TMEDA; t-BuLi / diethyl ether; pentane / 13 h / 20 °C

2.2: 75 percent / diethyl ether; pentane / 0.5 h / 20 °C

3.1: 92 percent / BF₃*OEt₂ / tetrahydrofuran / 3 h / 20 °C

4.1: chiral phosphite ligand; catecholborane / [Ph(COD)2]BF₄ / 1,2-dimethoxy-ethane / 2.5 h / -45 °C

4.2: 1,2-dimethoxy-ethane; tetrahydrofuran / -45 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / -90 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -90 - 20 °C

7.1: sec-BuLi / tetrahydrofuran; cyclohexane / 3 h / -78 - -10 °C

7.2: sodium acetate / [Pd(dppf)Cl₂]*CH₂Cl₂ / tetrahydrofuran; cyclohexane / -10 °C

7.3: tetrahydrofuran; cyclohexane / 24 h / 85 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; chiral phosphite ligand; boron trifluoride diethyl etherate; tert.-butyl lithium; sec.-butyllithium; benzo[1,3,2]dioxaborole; [Ph(COD)2]BF₄; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; cyclohexane; pentane;
DOI:10.1021/ol071228v