tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether

Base Information

• Chemical Name: tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether
• CAS No.: 347392-32-9
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602
• Mol file: 347392-32-9.mol

Synonyms:tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether

Chemical Property of tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether

There total 1 articles about tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether 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: 60.0%

1-(4-methoxyphenyl)ethanone (100-06-1) + (E:Z)-tert-butyldimethyl-[3-(2-bromophenyl)allyloxy]silane → tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether (347392-32-9)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; at 90 ℃; for 3h;

DOI:10.1021/jo0011991

Reference yield: 81.0%

tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether (347392-32-9) → 2-(2-oxo-[4'-methoxy-phenyl]-ethyl)-cinnamyl alcohol (347392-61-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1021/jo0011991

Reference yield:

tert-butyl-dimethylsilyl-2-(2-oxo-[4'-methoxyphenyl]-ethyl)-cinnamyl ether (347392-32-9) → 1-vinyl-3-(4'-methoxy-phenyl)-1H-isochromene

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 8 h / 20 °C

2: 88 percent / triethylamine / ethyl acetate; CH₂Cl₂ / 2 h / 20 °C

3: 20 percent / SEMI-ESPHOS; LHMDS / tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 18 h / 20 °C

With Semi-esphos; tetrabutyl ammonium fluoride; triethylamine; lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo0011991

upstream raw materials:

1-(4-methoxyphenyl)ethanone

Downstream raw materials:

2-(2-oxo-[4'-methoxy-phenyl]-ethyl)-cinnamyl alcohol

2-(2-oxo-[4'-methoxy-phenyl]-ethyl)-cinnamyl acetate