ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate

Base Information

• Chemical Name: ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate
• CAS No.: 145099-78-1
• Molecular Formula: C₁₈H₂₈O₃Si
• Molecular Weight: 320.504
• Mol file: 145099-78-1.mol

Synonyms:ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate

Chemical Property of ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate

There total 3 articles about ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate 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: 56.0%

phenylmagnesium bromide + ethyl (E)-4-(tert-butyldimethylsilyloxy)-2-iodo-2-butenoate (144079-81-2) → ethyl (Z)-2,4-diphenyl-2-butenoate (145099-82-7) + ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate (145099-78-1)

Guidance literature:

With zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1) -23 deg C, 3.5 h, 2) room temperature, 16 h;

DOI:10.1016/S0040-4020(01)89453-9

Reference yield:

tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate (145099-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) MeLi / 1a) THF, Et₂O, -78 deg C, 1 h, b) -20 deg C, 1 h, 2a) -20 deg C, 1 h, b) room temperature, 2 h

2: 1) Bu₃SnH, 2) I₂ / 1) Pd(PPh₃)4 / 1) THF, room temperature, 4 h, 2) CH₂Cl₂, 20 deg C

3: 56 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran / 1) -23 deg C, 3.5 h, 2) room temperature, 16 h

With methyllithium; iodine; tri-n-butyl-tin hydride; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89453-9

Reference yield:

ethyl 4-((tert-butyldimethylsilyl)oxy)but-2-ynoate (80866-51-9) → ethyl (Z)-4-(tert-butyldimethylsilyloxy)-2-phenyl-2-butenoate (145099-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Bu₃SnH, 2) I₂ / 1) Pd(PPh₃)4 / 1) THF, room temperature, 4 h, 2) CH₂Cl₂, 20 deg C

2: 56 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran / 1) -23 deg C, 3.5 h, 2) room temperature, 16 h

With iodine; tri-n-butyl-tin hydride; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89453-9

upstream raw materials:

ethyl (E)-4-(tert-butyldimethylsilyloxy)-2-iodo-2-butenoate

tert-Butyldimethyl(prop-2-ynyloxy)silane

ethyl 4-((tert-butyldimethylsilyl)oxy)but-2-ynoate

Downstream raw materials:

3-phenyl-2(5H)-furanone