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
Hs Code.:

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

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

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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%

: 936021-37-3
ethyl 3-hydroxy-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 936021-38-4
ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

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

: 936021-38-4
ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

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:

: 615-43-0
2-iodophenylamine

: 936021-38-4
ethyl 3-(tert-butyldimethylsilyloxy)-7-[2-(trimethylsilylethynyl)phenyl]hept-6-ynoate

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