1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

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Chemical Name:1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene
CAS No.:403696-77-5
Molecular Formula:C₃₄H₅₆O₃Si₂
Molecular Weight:568.988
Hs Code.:

1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-[1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

Synonyms:1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

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Chemical Property of 1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

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Technology Process of 1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

There total 18 articles about 1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene 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:

: 31558-41-5
4-bromo-2,5-dimethoxybenzaldehyde

: 403696-77-5
1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

Guidance literature:: Multi-step reaction with 11 steps

1.1: 100 percent / sodium borohydride / methanol / 0 - 20 °C

2.1: 95 percent / phosphorous tribromide / CH₂Cl₂ / 1 h / 0 - 20 °C

3.1: zinc; dibromoethane / tetrahydrofuran / 0.83 h / 0 °C

3.2: 98 percent / palladium tetrakis(triphenylphosphine) / tetrahydrofuran / 27 h / 23 °C

4.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 °C

4.2: 94 percent / diethyl ether / -78 - 35 °C

5.1: borontribromide / CH₂Cl₂ / 16 h / -78 - 23 °C

6.1: 5.53 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: tert-butyllithium / diethyl ether; pentane / 1 h / -78 °C

7.2: ZnBr₂; (1S,2R)-N-methylephedrine; n-butyllithium / diethyl ether; toluene; hexane / 1 h / 0 °C

7.3: 91 percent / toluene; diethyl ether / 1 h / 0 °C

8.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

9.1: H₂; quinoline / Pd/BaSO₄ / methanol; hexane / 4.67 h / 23 °C / 760.05 Torr

10.1: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C

10.2: 18 h / 23 °C

11.1: imidazole / dimethylformamide / 0 - 23 °C

11.2: 0.69 g / 17 h / 23 °C

With 1H-imidazole; quinoline; sodium tetrahydroborate; n-butyllithium; 1,1-Dibromoethane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; boron tribromide; phosphorus tribromide; N-ethyl-N,N-diisopropylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane; 9.1: Lindlar hydrogenation;
DOI:10.1021/ja016585u

Reference yield:

: 403696-81-1
5-(triisopropylsilyl)-4-pentyn-1-al

: 403696-77-5
1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 2.044 g / tetrahydrofuran / 0.17 h / -20 °C

2.1: zinc; dibromoethane / tetrahydrofuran / 0.83 h / 0 °C

2.2: 98 percent / palladium tetrakis(triphenylphosphine) / tetrahydrofuran / 27 h / 23 °C

3.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 °C

3.2: 94 percent / diethyl ether / -78 - 35 °C

4.1: borontribromide / CH₂Cl₂ / 16 h / -78 - 23 °C

5.1: 5.53 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: tert-butyllithium / diethyl ether; pentane / 1 h / -78 °C

6.2: ZnBr₂; (1S,2R)-N-methylephedrine; n-butyllithium / diethyl ether; toluene; hexane / 1 h / 0 °C

6.3: 91 percent / toluene; diethyl ether / 1 h / 0 °C

7.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

8.1: H₂; quinoline / Pd/BaSO₄ / methanol; hexane / 4.67 h / 23 °C / 760.05 Torr

9.1: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C

9.2: 18 h / 23 °C

10.1: imidazole / dimethylformamide / 0 - 23 °C

10.2: 0.69 g / 17 h / 23 °C

With 1H-imidazole; quinoline; n-butyllithium; 1,1-Dibromoethane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; boron tribromide; N-ethyl-N,N-diisopropylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane; 8.1: Lindlar hydrogenation;
DOI:10.1021/ja016585u

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 403696-77-5
1-(tert-butyl-dimethyl-silanyloxy)-2-[1-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hexa-2,5-dienyl]-4-methoxy-5-(2-methyl-hept-2-en-6-ynyl)-benzene

Guidance literature:: Multi-step reaction with 12 steps

1.1: ethylmagnesium chloride / tetrahydrofuran / 12 h / Heating

1.2: 94 percent / tetrahydrofuran / 6 h / Heating

2.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h / 20 °C

3.1: 2.044 g / tetrahydrofuran / 0.17 h / -20 °C

4.1: zinc; dibromoethane / tetrahydrofuran / 0.83 h / 0 °C

4.2: 98 percent / palladium tetrakis(triphenylphosphine) / tetrahydrofuran / 27 h / 23 °C

5.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 °C

5.2: 94 percent / diethyl ether / -78 - 35 °C

6.1: borontribromide / CH₂Cl₂ / 16 h / -78 - 23 °C

7.1: 5.53 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: tert-butyllithium / diethyl ether; pentane / 1 h / -78 °C

8.2: ZnBr₂; (1S,2R)-N-methylephedrine; n-butyllithium / diethyl ether; toluene; hexane / 1 h / 0 °C

8.3: 91 percent / toluene; diethyl ether / 1 h / 0 °C

9.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

10.1: H₂; quinoline / Pd/BaSO₄ / methanol; hexane / 4.67 h / 23 °C / 760.05 Torr

11.1: tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C

11.2: 18 h / 23 °C

12.1: imidazole / dimethylformamide / 0 - 23 °C

12.2: 0.69 g / 17 h / 23 °C

With 1H-imidazole; quinoline; n-butyllithium; 1,1-Dibromoethane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; ethylmagnesium chloride; boron tribromide; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane; 10.1: Lindlar hydrogenation;
DOI:10.1021/ja016585u