Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate

Base Information

• Chemical Name: Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate
• CAS No.: 158469-52-4
• Molecular Formula: C₂₇H₂₈O₅S
• Molecular Weight: 464.582
• Mol file: 158469-52-4.mol

Synonyms:Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate

Chemical Property of Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate

There total 8 articles about Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate 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: 79.0%

(Z)-ethyl 3-(tributylstannyl)propenoate (82101-76-6,106335-84-6,128266-87-5) + 3-<4-(5-Iodo-2-methoxyphenoxy)phenyl>-3-(phenylsulfanyl)propan-1-ol (158469-51-3) → Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate (158469-52-4)

Guidance literature:

With palladium diacetate; In various solvent(s); 1.) r.t., 30 min, 2.) 25 deg C, 40 h;

DOI:10.1021/jo00097a052

Reference yield:

4-bromobenzenecarbonitrile (623-00-7) → Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate (158469-52-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / K₂CO₃, CuO, pyridine / 21 h / 120 °C

2: 80 percent / H₅IO₆, I₂, aq. H₂SO₄ / acetic acid / 2 h / 90 °C

3: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 7 h / -78 °C

4: 94 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran; toluene / 1.) -78 deg C, 10 min, 2.) -78 deg C, 10 h

5: 94 percent / DBU / tetrahydrofuran / 30 h / Heating

6: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 1.) -78 deg, 2 h, 2.) ice-bath cooling, 30 min

7: 79 percent / Pd(OAc)2 / various solvent(s) / 1.) r.t., 30 min, 2.) 25 deg C, 40 h

With pyridine; palladium diacetate; 18-crown-6 ether; sulfuric acid; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; copper(II) oxide; In tetrahydrofuran; diethyl ether; cyclohexane; acetic acid; toluene;

DOI:10.1021/jo00097a052

Reference yield:

4-(2'-methoxyphenoxy)benzonitrile (78338-67-7) → Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate (158469-52-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / H₅IO₆, I₂, aq. H₂SO₄ / acetic acid / 2 h / 90 °C

2: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 7 h / -78 °C

3: 94 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran; toluene / 1.) -78 deg C, 10 min, 2.) -78 deg C, 10 h

4: 94 percent / DBU / tetrahydrofuran / 30 h / Heating

5: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 1.) -78 deg, 2 h, 2.) ice-bath cooling, 30 min

6: 79 percent / Pd(OAc)2 / various solvent(s) / 1.) r.t., 30 min, 2.) 25 deg C, 40 h

With palladium diacetate; 18-crown-6 ether; sulfuric acid; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; In tetrahydrofuran; diethyl ether; cyclohexane; acetic acid; toluene;

DOI:10.1021/jo00097a052

upstream raw materials:

(Z)-ethyl 3-(tributylstannyl)propenoate

3-<4-(5-Iodo-2-methoxyphenoxy)phenyl>-3-(phenylsulfanyl)propan-1-ol

4-bromobenzenecarbonitrile

4-(2'-methoxyphenoxy)benzonitrile

Downstream raw materials:

3-<3-<4-(3-Hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>propionic acid

4-Methoxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

combretastatin D-2