ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

Base Information

• Chemical Name: ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate
• CAS No.: 936021-38-4
• Molecular Formula: C₂₆H₄₀O₃Si₂
• Molecular Weight: 456.773
• Mol file: 936021-38-4.mol

Synonyms:ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

Chemical Property of ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

There total 6 articles about ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate 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: 90.0%

ethyl 3-hydroxy-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate (936021-37-3) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate (936021-38-4)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ja064470q

Reference yield:

3,3-diethyl-1-[2-(trimethylsilylethynyl)phenyl]triaz-1-ene → ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate (936021-38-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 8.670 g / MeI / 20 h / 145 °C

2.1: Pd(PPh₃)2Cl₂; CuI / tetrahydrofuran / 0.08 h

2.2: 98 percent / NEt₃; PPh₃ / tetrahydrofuran / 16 h

3.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h

4.1: LDA / tetrahydrofuran / 1 h / -78 °C

4.2: 90 percent / tetrahydrofuran / 0.5 h / -78 °C

5.1: 90 percent / imidazole; DMAP / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; dmap; Dess-Martin periodane; lithium diisopropyl amide; methyl iodide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane; 3.1: Des-Martin oxidation;

DOI:10.1021/ja064470q

Reference yield:

2-iodophenylamine (615-43-0) → ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate (936021-38-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aq. HCl / 0.17 h / Heating

1.2: aq. NaNO₂ / 0.33 h / -5 °C

1.3: 94 percent / H₂O / -5 - 20 °C

2.1: Pd(PPh₃)2Cl₂; CuI / tetrahydrofuran / 0.08 h

2.2: NEt₃; PPh₃ / tetrahydrofuran / 18 h

3.1: 8.670 g / MeI / 20 h / 145 °C

4.1: Pd(PPh₃)2Cl₂; CuI / tetrahydrofuran / 0.08 h

4.2: 98 percent / NEt₃; PPh₃ / tetrahydrofuran / 16 h

5.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h

6.1: LDA / tetrahydrofuran / 1 h / -78 °C

6.2: 90 percent / tetrahydrofuran / 0.5 h / -78 °C

7.1: 90 percent / imidazole; DMAP / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; Dess-Martin periodane; lithium diisopropyl amide; methyl iodide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane; 5.1: Des-Martin oxidation;

DOI:10.1021/ja064470q

upstream raw materials:

ethyl 3-hydroxy-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

tert-butyldimethylsilyl chloride

2-iodophenylamine

1-iodo-2-ethynylbenzene

Downstream raw materials:

3-(tert-butyldimethylsilyloxy)-7-[2-(iodoethynyl)phenyl]hept-6-ynal