3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone

Base Information

• Chemical Name: 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone
• CAS No.: 76042-92-7
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• Mol file: 76042-92-7.mol

Synonyms:3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone

Chemical Property of 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone

There total 14 articles about 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone 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: 44.0%

2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran (74275-68-6) → 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone (76042-92-7)

Guidance literature:

bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾; In 1,4-dioxane; for 10h; Heating;

DOI:10.1021/ja00547a015

Reference yield:

hexanal (66-25-1) → 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone (76042-92-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) reflux, overnight

2: 63 percent / 0.5 M hydrochloric acid / tetrahydrofuran / 24 h

3: 70 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

4: 1.) phosphorus oxychloride, HMPA, 2.) pyridine / 1.) room temperature -> 50 deg C, 2.) 50 deg C -> 100 deg C

5: 73 percent / DIBAL-H, n-butyllithium / tetrahydrofuran; hexane / -78 °C

6: 1.83 g / 48percent fluoboric acid / diethyl ether

7: 85 percent / lithium diisopropyl amide / diethyl ether / -78 °C

8: MCPBA / CH₂Cl₂ / 12 h / Ambient temperature

9: magnesium methoxide / methanol / Ambient temperature

10: 150 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

11: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, room temperature, 45 min, 2.) reflux, 4.5 h

12: 44 percent / bis<1,2-bis(diphenylphosphino)ethane>palladium⁽⁰⁾ / dioxane / 10 h / Heating

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrafluoroboric acid; n-butyllithium; sodium hydride; diisobutylaluminium hydride; magnesium methanolate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja00547a015

Reference yield:

benzyl bromide (100-39-0) → 3-<(E)-3-(benzyloxy)-1-octenyl>cyclopentanone (76042-92-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) reflux, overnight

2: 63 percent / 0.5 M hydrochloric acid / tetrahydrofuran / 24 h

3: 70 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

4: 1.) phosphorus oxychloride, HMPA, 2.) pyridine / 1.) room temperature -> 50 deg C, 2.) 50 deg C -> 100 deg C

5: 73 percent / DIBAL-H, n-butyllithium / tetrahydrofuran; hexane / -78 °C

6: 1.83 g / 48percent fluoboric acid / diethyl ether

7: 85 percent / lithium diisopropyl amide / diethyl ether / -78 °C

8: MCPBA / CH₂Cl₂ / 12 h / Ambient temperature

9: magnesium methoxide / methanol / Ambient temperature

10: 150 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

11: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, room temperature, 45 min, 2.) reflux, 4.5 h

12: 44 percent / bis<1,2-bis(diphenylphosphino)ethane>palladium⁽⁰⁾ / dioxane / 10 h / Heating

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrafluoroboric acid; n-butyllithium; sodium hydride; diisobutylaluminium hydride; magnesium methanolate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja00547a015

upstream raw materials:

2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

cyclopent-2-enone

{[(1-pentylprop-2-ynyl)oxy]methyl}benzene

benzyl bromide