3-Butyn-2-ol, 2-methyl-4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-

Base Information

• Chemical Name: 3-Butyn-2-ol, 2-methyl-4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-
• CAS No.: 119754-13-1
• Molecular Formula: C16H20O3
• Molecular Weight: 260.333
• DSSTox Substance ID: DTXSID20470741
• Mol file: 119754-13-1.mol

Synonyms:3-Butyn-2-ol, 2-methyl-4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-;119754-13-1;DTXSID20470741

Chemical Property of 3-Butyn-2-ol, 2-methyl-4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 260.14124450
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C#CC1=CC=C(C=C1)OC2CCCCO2)O

Technology Process of 3-Butyn-2-ol, 2-methyl-4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-

There total 7 articles about 3-Butyn-2-ol, 2-methyl-4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]- 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: 95.0%

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene (36603-49-3) + 2-methyl-but-3-yn-2-ol (115-19-5) → 1-[(tetrahydro-2H-pyran-2-yl)oxy]-4-[3-hydroxy-3-methylbut-1-ynyl]benzene (119754-13-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.07.144

Reference yield: 93.0%

2-methyl-but-3-yn-2-ol (115-19-5) + 4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene (99522-34-6) → 1-[(tetrahydro-2H-pyran-2-yl)oxy]-4-[3-hydroxy-3-methylbut-1-ynyl]benzene (119754-13-1)

Guidance literature:

4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene; With copper(l) iodide; triphenylphosphine; palladium dichloride; triethylamine; at 50 ℃; for 0.5h;

2-methyl-but-3-yn-2-ol; at 85 ℃; for 5h;

Reference yield:

p-Iodophenol (540-38-5) → 1-[(tetrahydro-2H-pyran-2-yl)oxy]-4-[3-hydroxy-3-methylbut-1-ynyl]benzene (119754-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / PPTS / CH₂Cl₂ / 12 h / 20 °C

2: 80 percent / CuI; PPh₃; NEt₃ / (PPh₃)2PdCl₂ / 16 h / 65 °C

With copper(l) iodide; pyridinium p-toluenesulfonate; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; 1: Addition / 2: Alkylation;

DOI:10.1039/a907974b

upstream raw materials:

2-methyl-but-3-yn-2-ol

4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene

3,4-dihydro-2H-pyran

p-Iodophenol

Downstream raw materials:

[4-(tetrahydropyran-2-yloxy)phenyl]ethyne

4-ethynylphenol

4-(4-hexyl-phenylethynyl)-phenol

2-[4-(4-hexyl-phenylethynyl)-phenoxy]-tetrahydro-pyran