(E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate

Base Information

• Chemical Name: (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate
• CAS No.: 783332-95-6
• Molecular Formula: C₂₀H₃₂O₄Si
• Molecular Weight: 364.557
• Mol file: 783332-95-6.mol

Synonyms:(E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate

Chemical Property of (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate

There total 2 articles about (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate 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: 91.0%

methyl chloroformate (79-22-1) + (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-en-1-ol (783332-96-7) → (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate (783332-95-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ja048078t

Reference yield:

5-[2-(tert-butyl-dimethyl-silanyloxy)-5-methyl-phenyl]-pent-2-enoic acid methyl ester → (E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate (783332-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / -78 - 20 °C

2: 91 percent / DMAP; pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja048078t

Reference yield: 93.0%

(E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-enyl methyl carbonate (783332-95-6) → (E)-5-(2-hydroxy-5-methylphenyl)pent-2-enyl methyl carbonate (593251-67-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ja048078t

upstream raw materials:

methyl chloroformate

(E)-5-(2-tert-butyldimethylsiloxy-5-methylphenyl)pent-2-en-1-ol

Downstream raw materials:

(E)-5-(2-hydroxy-5-methylphenyl)pent-2-enyl methyl carbonate