[5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

Base Information

Chemical Name:[5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone
CAS No.:852380-74-6
Molecular Formula:C₂₈H₄₅NO₄Si₂
Molecular Weight:515.841
Hs Code.:

[5-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-indol-2-yl]-methanone

Synonyms:[5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

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Chemical Property of [5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

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Technology Process of [5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

There total 11 articles about [5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone 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: 36.0%

: 852380-73-5
2-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

: 756893-86-4
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methoxy-methyl-amide

: 852380-74-6
[5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

Guidance literature:: 2-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methoxy-methyl-amide; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;
DOI:10.1021/ja050586v

Reference yield:

: 852380-48-4
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

: 852380-74-6
[5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

2.1: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 36 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

With n-butyllithium; hydrogen; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ja050586v

Reference yield:

: 852380-64-4
(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

: 852380-74-6
[5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-2-yl]-methanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / triethylamine; DMAP / CH₂Cl₂ / 0.17 h / 23 °C

2.1: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C

3.1: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

4.1: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

5.2: 36 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

With triethylsilane; dmap; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; hydrogen; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ja050586v