Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester
• CAS No.: 201345-78-0
• Molecular Formula: C₁₈H₁₆O₅S
• Molecular Weight: 344.388
• Mol file: 201345-78-0.mol

Synonyms:Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester

Chemical Property of Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester

There total 4 articles about Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl 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: 86.0%

p-toluenesulfonyl chloride (98-59-9) + 4-Benzo[1,3]dioxol-5-yl-but-2-yn-1-ol (290362-00-4) → Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester (201345-78-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -40 ℃;

DOI:10.1016/S0040-4039(00)00604-3

Reference yield:

piperonal (120-57-0,30024-74-9) → Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester (201345-78-0)

Guidance literature:

Multi-step reaction with 4 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: Et₃N; DMAP / CH₂Cl₂

3: 69 percent / Et₃SiH; TFA / CH₂Cl₂ / -20 °C

4: 86 percent / n-BuLi / tetrahydrofuran / -40 °C

With triethylsilane; dmap; n-butyllithium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Acetylation / 3: Reduction / 4: Tosylation;

DOI:10.1016/S0040-4039(00)00604-3

Reference yield:

1-benzo[1,3]dioxol-5-yl-4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol → Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester (201345-78-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; DMAP / CH₂Cl₂

2: 69 percent / Et₃SiH; TFA / CH₂Cl₂ / -20 °C

3: 86 percent / n-BuLi / tetrahydrofuran / -40 °C

With triethylsilane; dmap; n-butyllithium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: Reduction / 3: Tosylation;

DOI:10.1016/S0040-4039(00)00604-3

upstream raw materials:

p-toluenesulfonyl chloride

4-Benzo[1,3]dioxol-5-yl-but-2-yn-1-ol

piperonal

acetic acid 1-benzo[1,3]dioxol-5-yl-4-(tetrahydro-pyran-2-yloxy)-but-2-ynyl ester

Downstream raw materials:

acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester

acetic acid 4-(3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl)-3-hydroxy-phenyl ester

anolignan A