(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

Base Information

Chemical Name:(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne
CAS No.:619309-10-3
Molecular Formula:C₂₅H₂₉ClSi₂
Molecular Weight:421.129
Hs Code.:

Synonyms:(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

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Chemical Property of (E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

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Technology Process of (E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

There total 4 articles about (E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne 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: 98.0%

: 619309-04-5
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

: 619309-10-3
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;
DOI:10.1021/ol035536e

Reference yield:

: 619308-84-8
5-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)penta-1,3-diyne

: 619309-10-3
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

Guidance literature:: Multi-step reaction with 4 steps

1.1: Me₃SnLi; CuBr*Me₂S complex / tetrahydrofuran / -50 - 20 °C

1.2: n-BuLi / tetrahydrofuran; hexane / 4 h / -78 °C

1.3: CuCl₂ / tetrahydrofuran / 0 - 20 °C

2.1: 89 percent / MnO₂ / CH₂Cl₂ / 5 h / 20 °C

3.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 76 percent / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 98 percent / LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

With (trimethylstannyl)lithium; manganese(IV) oxide; copper(I) bromide dimethylsulfide complex; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.2: 1,4-retro-Brook rearrangement;
DOI:10.1021/ol035536e

Reference yield:

: 619308-98-4
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-pent-3-en-1-yn-5-al

: 619309-10-3
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-hex-3-en-1,5diyne

Guidance literature:: Multi-step reaction with 2 steps

1.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 76 percent / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 98 percent / LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

With triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol035536e