(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester
CAS No.:886580-13-8
Molecular Formula:C₁₇H₂₆O₃Si
Molecular Weight:306.477
Hs Code.:

Synonyms:(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

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Chemical Property of (E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

Chemical Property:

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Technology Process of (E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

There total 1 articles about (E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl 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: 60.0%

: 5927-18-4
trimethyl phosphonoacetate

: 103548-04-5
2-(tert-butyldimethylsilanyloxy)-1-phenylethan-1-one

: (Z)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

: 886580-13-8
(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

Guidance literature:: trimethyl phosphonoacetate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2-(tert-butyldimethylsilanyloxy)-1-phenylethan-1-one; In tetrahydrofuran; hexane; at 20 ℃; for 5h;
DOI:10.1016/j.bmc.2005.12.040

Reference yield:

: 886580-13-8
(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

: 2,3-dibromo-4-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-butyric acid methyl ester

Guidance literature:: With bromine; In dichloromethane; at -78 ℃; for 12h;
DOI:10.1016/j.bmc.2005.12.040

Reference yield:

: 886580-13-8
(E)-4-(tert-butyldimethylsilyloxy)-3-phenylbut-2-enoic acid methyl ester

: (E)-2-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]deca-3,9-diyn-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: bromine / CH₂Cl₂ / 12 h / -78 °C

2: triethylamine / CH₂Cl₂ / 38 h / -78 °C

3: 96 percent / diisobutylaluminium hydride / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

4: triethylamine; CuI / Pd(PPh₃)4 / acetonitrile / 18 h / Heating

With copper(l) iodide; bromine; diisobutylaluminium hydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile; 4: Sonogashira coupling;
DOI:10.1016/j.bmc.2005.12.040