(E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol

Base Information

• Chemical Name: (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol
• CAS No.: 952156-39-7
• Molecular Formula: C₁₇H₃₀OSi
• Molecular Weight: 278.51
• Mol file: 952156-39-7.mol

Synonyms:(E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol

Chemical Property of (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol

There total 4 articles about (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol 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: 81.0%

tert-butyl (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}acrylate (952156-32-0) → (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol (952156-39-7)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 - 22 ℃; for 6h;

DOI:10.1002/ejoc.200700201

Reference yield:

2-bromocyclohexanone (1056477-06-5,822-85-5) → (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol (952156-39-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium bis(trimethylsilyl)amide / diethyl ether / 0.5 h / -78 °C

1.2: 94 percent / diethyl ether / 24 h / -78 - 22 °C

2.1: 80 percent / LiCl / tetrakis(triphenylphosphane)palladium / dimethylformamide / 12 h / 90 °C

3.1: 78 percent / PPh₃; NEt₃ / Pd(OAc)2 / dimethylformamide / 14 h / 90 °C

4.1: 81 percent / diisobutylaluminum hydride / toluene / 6 h / -78 - 22 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; N,N-dimethyl-formamide; toluene; 2.1: Stille coupling / 3.1: Heck reaction;

DOI:10.1002/ejoc.200700201

Reference yield:

[(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane (952156-26-2) → (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol (952156-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / PPh₃; NEt₃ / Pd(OAc)2 / dimethylformamide / 14 h / 90 °C

2: 81 percent / diisobutylaluminum hydride / toluene / 6 h / -78 - 22 °C

With diisobutylaluminium hydride; triethylamine; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; toluene; 1: Heck reaction;

DOI:10.1002/ejoc.200700201

upstream raw materials:

tert-butyl (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}acrylate

2-bromocyclohexanone

[(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane

1-bromo-2-trifluoromethanesulfonyloxycyclohexene

Downstream raw materials:

(E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)silane