4,6-Undecadienoic acid, 10-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, ethyl ester, (4E,6Z,10S)-

Base Information

Chemical Name:4,6-Undecadienoic acid, 10-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, ethyl ester, (4E,6Z,10S)-
CAS No.:668461-30-1
Molecular Formula:C29H40O3Si
Molecular Weight:464.72
Hs Code.:

Synonyms:

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Chemical Property of 4,6-Undecadienoic acid, 10-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, ethyl ester, (4E,6Z,10S)-

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Technology Process of 4,6-Undecadienoic acid, 10-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, ethyl ester, (4E,6Z,10S)-

There total 10 articles about 4,6-Undecadienoic acid, 10-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, ethyl ester, (4E,6Z,10S)- 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: 94.0%

: 203387-39-7
ethyl (4E,10S)-10-(tert-butyl(diphenyl)silyloxy)undec-4-en-6-ynoate

: 668461-30-1
ethyl (4E,6Z,10S)-10-(tert-butyl(diphenyl)silyloxy)undeca-4,6-dienoate

Guidance literature:: With ethylene dibromide; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/jo035391p

Reference yield:

: 102732-44-5
ethyl (S)-2-(tert-butyldiphenylsilyloxy)propanoate

: 668461-30-1
ethyl (4E,6Z,10S)-10-(tert-butyl(diphenyl)silyloxy)undeca-4,6-dienoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

2.1: NaH / tetrahydrofuran / 2 h

2.2: 75 percent / diethyl ether / 16 h / 22 °C

3.1: 83 percent / H₂; Raney nickel / methanol / 4500.36 Torr

4.1: 94 percent / DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

5.1: triphenylphosphine; Zn / CH₂Cl₂ / 16 h / 20 °C

5.2: 75 percent / pyridine / CH₂Cl₂ / 2 h

6.1: 91 percent / Mg; 1,2-dibromoethane / tetrahydrofuran / Heating

7.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

7.2: LiBr / tetrahydrofuran; hexane / 0.33 h / 20 °C

7.3: 89 percent / tetrahydrofuran; hexane / 2 h / -78 °C

8.1: propionic acid / xylene / 2 h / Heating

9.1: 94 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

With n-butyllithium; hydrogen; nickel; sodium hydride; diisobutylaluminium hydride; magnesium; propionic acid; ethylene dibromide; triphenylphosphine; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; xylene; 2.1: Horner-Wadsworth-Simmons olefination / 8.1: Johnson-Claisen rearrangement;
DOI:10.1021/jo035391p

Reference yield:

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 668461-30-1
ethyl (4E,6Z,10S)-10-(tert-butyl(diphenyl)silyloxy)undeca-4,6-dienoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 2 h

1.2: 75 percent / diethyl ether / 16 h / 22 °C

2.1: 83 percent / H₂; Raney nickel / methanol / 4500.36 Torr

3.1: 94 percent / DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

4.1: triphenylphosphine; Zn / CH₂Cl₂ / 16 h / 20 °C

4.2: 75 percent / pyridine / CH₂Cl₂ / 2 h

5.1: 91 percent / Mg; 1,2-dibromoethane / tetrahydrofuran / Heating

6.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: LiBr / tetrahydrofuran; hexane / 0.33 h / 20 °C

6.3: 89 percent / tetrahydrofuran; hexane / 2 h / -78 °C

7.1: propionic acid / xylene / 2 h / Heating

8.1: 94 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

With n-butyllithium; hydrogen; nickel; sodium hydride; diisobutylaluminium hydride; magnesium; propionic acid; ethylene dibromide; triphenylphosphine; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; xylene; 1.1: Horner-Wadsworth-Simmons olefination / 7.1: Johnson-Claisen rearrangement;
DOI:10.1021/jo035391p