2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran

Base Information

• Chemical Name: 2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran
• CAS No.: 908125-17-7
• Molecular Formula: C₂₃H₃₂O₂
• Molecular Weight: 340.506
• Mol file: 908125-17-7.mol

Synonyms:2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran

Chemical Property of 2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran

There total 2 articles about 2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran 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:

{3,3-dimethyl-5-[4-(tetrahydro-pyran-2-yloxy)-butyl]-hex-5-en-1-ynyl}-triisopropyl-silane + iodobenzene (591-50-4) → 2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran (908125-17-7)

Guidance literature:

{3,3-dimethyl-5-[4-(tetrahydro-pyran-2-yloxy)-butyl]-hex-5-en-1-ynyl}-triisopropyl-silane; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Heating;

iodobenzene; With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ja051110e

Reference yield:

2-(5-bromomethyl-hex-5-enyloxy)-tetrahydro-pyran → 2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran (908125-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; TMEDA / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: TBAF / tetrahydrofuran / 1 h / Heating

2.2: CuI / PdCl₂(PPh₃)2 / tetrahydrofuran / 2 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 2.2: Sonogashira reaction;

DOI:10.1021/ja051110e

Reference yield: 72.0%

2-(7,7-dimethyl-5-methylene-9-phenyl-non-8-ynyloxy)-tetrahydro-pyran (908125-17-7) → 2-[4-(5,5-dimethyl-2-phenyl-cyclohexa-1,3-dienyl)-butoxy]-tetrahydro-pyran

Guidance literature:

platinum(II) chloride; In toluene; acetonitrile; at 80 ℃; for 12h;

DOI:10.1021/ja063384n

upstream raw materials:

iodobenzene

Downstream raw materials:

7,7-dimethyl-5-methylene-9-phenyl-non-8-yn-1-ol