[7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ⁵-phosphane

Base Information

• Chemical Name: [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ⁵-phosphane
• CAS No.: 86118-23-2
• Molecular Formula: C₃₁H₃₉OPSi
• Molecular Weight: 486.709

Synonyms:[7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ⁵-phosphane

Chemical Property of [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ⁵-phosphane

Chemical Property:

Purity/Quality:

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Technology Process of [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ⁵-phosphane

There total 8 articles about [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ⁵-phosphane 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:

(7-(tert-butyldimethylsiloxy)hepta-3,4-dien-1-yl)triphenylphosphonium iodide (86118-22-1) → [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ5-phosphane (86118-23-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 1h;

DOI:10.1021/jo00163a030

Reference yield:

4-(tert-butyldimethylsilyloxy)-1-butyne (78592-82-2) → [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ5-phosphane (86118-23-2)

Guidance literature:

Multi-step reaction with 8 steps

2: 50 percent / 1.) triethylamine, methanesulfonyl chloride, 2.) LiCl / Ambient temperature; 1.) CH₂Cl₂, 15 min, -20 deg C, 2.) DMF, 48 h, room temp.

3: 91 percent / H₂, quinoline / Lindlar cat. / ethanol / 760 Torr

4: 76 percent / 50percent KOH, n-Bu₄NBr / 3 h

5: 84 percent / n-BuLi / diethyl ether / 1 h / -70 °C

6: 98 percent / NaI / acetone / 24 h / Heating

7: 70 percent / acetonitrile / 3 h / Heating

8: n-BuLi / tetrahydrofuran / 1 h / -70 °C

With quinoline; potassium hydroxide; n-butyllithium; tetrabutylammomium bromide; hydrogen; methanesulfonyl chloride; triethylamine; sodium iodide; lithium chloride; Lindlar catalyst; In tetrahydrofuran; diethyl ether; ethanol; acetone; acetonitrile;

DOI:10.1021/jo00163a030

Reference yield:

6-chloro-3-hexyn-1-yl tert-butyldimethylsilyl ether (86118-36-7) → [7-(tert-Butyl-dimethyl-silanyloxy)-hepta-3,4-dienylidene]-triphenyl-λ5-phosphane (86118-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / H₂, quinoline / Lindlar cat. / ethanol / 760 Torr

2: 76 percent / 50percent KOH, n-Bu₄NBr / 3 h

3: 84 percent / n-BuLi / diethyl ether / 1 h / -70 °C

4: 98 percent / NaI / acetone / 24 h / Heating

5: 70 percent / acetonitrile / 3 h / Heating

6: n-BuLi / tetrahydrofuran / 1 h / -70 °C

With quinoline; potassium hydroxide; n-butyllithium; tetrabutylammomium bromide; hydrogen; sodium iodide; Lindlar catalyst; In tetrahydrofuran; diethyl ether; ethanol; acetone; acetonitrile;

DOI:10.1021/jo00163a030

upstream raw materials:

(7-(tert-butyldimethylsiloxy)hepta-3,4-dien-1-yl)triphenylphosphonium iodide

4-(tert-butyldimethylsilyloxy)-1-butyne

(3Z)-6-chloro-3-hexen-1-yl tert-butyldimethylsilyl ether

6-chloro-3-hexyn-1-yl tert-butyldimethylsilyl ether

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