2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene

Base Information

• Chemical Name: 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene
• CAS No.: 166757-18-2
• Molecular Formula: C₁₇H₂₄OSi
• Molecular Weight: 272.462
• Mol file: 166757-18-2.mol

Synonyms:2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene

Chemical Property of 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene

There total 4 articles about 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene 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%

2-[2-(trimethylsilyl)ethynyl]benzaldehyde (77123-58-1) + bromopentene (1119-51-3) → 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene (166757-18-2)

Guidance literature:

bromopentene; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

2-[2-(trimethylsilyl)ethynyl]benzaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02703

Reference yield: 38.0%

2-((trimethylsilyl)ethnyl)benzaldehyde + 4-penten-1-ylmagnesium bromide (34164-50-6) → 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene (166757-18-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.8b08596

Reference yield:

trimethylsilylacetylene (1066-54-2) → 2-(1-Hydroxy-5-hexenyl)-1-<2-(trimethylsilyl)ethynyl>benzene (166757-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / triphenylphosphine, triethylamine, palladium(II) acetate, CuI / 5 h / 80 °C

2: 1.) magnesium / 1.) ether, r.t., 15 h, 2.) ether, r.t., 1 h

With copper(l) iodide; palladium diacetate; magnesium; triethylamine; triphenylphosphine;

DOI:10.1021/jo00122a047

upstream raw materials:

2-[2-(trimethylsilyl)ethynyl]benzaldehyde

bromopentene

trimethylsilylacetylene

ortho-bromobenzaldehyde

Downstream raw materials:

2-(1-Oxo-5-hexen-1-yl)-1-<2-(trimethylsilyl)ethynyl>benzene