Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester
• CAS No.: 205989-59-9
• Molecular Formula: C₂₃H₃₄O₆S
• Molecular Weight: 438.585
• Mol file: 205989-59-9.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester

There total 6 articles about Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester 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: 69.0%

p-toluenesulfonyl chloride (98-59-9) + (E)-1-Hydroxy-8-methyl-10-(tetrahydro-pyran-2-yloxy)-dec-8-en-5-one (205989-58-8) → Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester (205989-59-9)

Guidance literature:

With triethylamine; In dichloromethane; 0 deg C to 15 deg C, 1 h then r.t., 14 h;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester (205989-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / TsOH / CH₂Cl₂ / 0.5 h / 0 °C

2: 65 percent / 60percent NaH in oil, BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

3: 1.) NaOH; 2.) 1M Bu₄NF / 1.) MeOH, reflux, 30 min; 2.) THF, r.t., 2 h

4: 69 percent / triethylamine / CH₂Cl₂ / 0 deg C to 15 deg C, 1 h then r.t., 14 h

With sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

Reference yield:

4-bromo-3-methylbut-2-en-1-ol (59499-36-4) → Toluene-4-sulfonic acid (E)-8-methyl-5-oxo-10-(tetrahydro-pyran-2-yloxy)-dec-8-enyl ester (205989-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / TsOH / CH₂Cl₂ / 0.5 h / 0 °C

2: 65 percent / 60percent NaH in oil, BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

3: 1.) NaOH; 2.) 1M Bu₄NF / 1.) MeOH, reflux, 30 min; 2.) THF, r.t., 2 h

4: 69 percent / triethylamine / CH₂Cl₂ / 0 deg C to 15 deg C, 1 h then r.t., 14 h

With sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

upstream raw materials:

p-toluenesulfonyl chloride

(E)-1-Hydroxy-8-methyl-10-(tetrahydro-pyran-2-yloxy)-dec-8-en-5-one

3,4-dihydro-2H-pyran

4-bromo-3-methylbut-2-en-1-ol