ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate

Base Information

• Chemical Name: ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate
• CAS No.: 352431-93-7
• Molecular Formula: C₁₆H₂₄O₃Si
• Molecular Weight: 292.45
• Mol file: 352431-93-7.mol

Synonyms:ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate

Chemical Property of ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate

There total 6 articles about ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate 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: 94.0%

(E)-3-phenylpropenal (14371-10-9) + 1-ethoxy-1-(trimethylsiloxy)ethene (18295-66-4) → ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate (352431-93-7)

Guidance literature:

In toluene; at 23 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

DOI:10.3987/COM-09-S(S)133

Reference yield: 72.0%

chloro-trimethyl-silane (75-77-4) + (E)-ethyl 3-hydroxy-5-phenylpent-4-enoate (95728-97-5) → ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate (352431-93-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 17h;

DOI:10.1039/b010138i

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) + ethyl acetate (141-78-6) → ethyl trans-5-phenyl-3-trimethylsiloxypent-4-enoate (352431-93-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151192

upstream raw materials:

(E)-3-phenylpropenal

trimethylsilanyl-acetic acid ethyl ester

chloro-trimethyl-silane

(E)-ethyl 3-hydroxy-5-phenylpent-4-enoate

Downstream raw materials:

(1E,5Z)-5-Ethoxy-1-phenylhepta-1,5-dien-3-ol

(1E,5E)-5-Ethoxy-1-phenylhepta-1,5-dien-3-ol

(E)-ethyl 3-hydroxy-5-phenylpent-4-enoate

Refernces

• 1、 Downey, C. Wade,Dixon, Grant J.,Ingersoll, Jared A.,Fuller, Claire N.,MacCormac, Kenneth W.,Takashima, Anna,Sediqui, Rohina. "One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents". supporting information. . Retrieved 2019/10/14.
• 2、 Rutherford, Alistair P.,Gibb, Cameron S.,Hartley, Richard C.,Goodman, Jonathan M.. "Stereocontrol in a one-pot procedure for anionic oxy-Cope rearrangement followed by intramolecular aldol reaction". . p. 1051 - 1061. Retrieved 2007/10/03.