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

Base Information

Chemical Name:(E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)silane
CAS No.:952156-41-1
Molecular Formula:C₂₂H₃₈O₂Si
Molecular Weight:362.628
Hs Code.:

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

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

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

There total 5 articles about (E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)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: 97.0%

: 110-87-2
3,4-dihydro-2H-pyran

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

: 952156-41-1
(E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)silane

Guidance literature:: With scandium tris(trifluoromethanesulfonate); In ethyl acetate; at 20 ℃; for 1h;
DOI:10.1002/ejoc.200700201

Reference yield:

: 1056477-06-5,822-85-5
2-bromocyclohexanone

: 952156-41-1
(E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)silane

Guidance literature:: Multi-step reaction with 5 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

5.1: 97 percent / scandium(III) trifluoromethanesulfonate / ethyl acetate / 1 h / 20 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; scandium tris(trifluoromethanesulfonate); palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Stille coupling / 3.1: Heck reaction;
DOI:10.1002/ejoc.200700201

Reference yield:

: 952156-26-2
[(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane

: 952156-41-1
(E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)silane

Guidance literature:: Multi-step reaction with 3 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

3: 97 percent / scandium(III) trifluoromethanesulfonate / ethyl acetate / 1 h / 20 °C

With diisobutylaluminium hydride; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate); palladium diacetate; In ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Heck reaction;
DOI:10.1002/ejoc.200700201