3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane

Base Information

• Chemical Name: 3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane
• CAS No.: 758692-17-0
• Molecular Formula: C₂₃H₂₈O₂
• Molecular Weight: 336.474
• Mol file: 758692-17-0.mol

Synonyms:3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane

Chemical Property of 3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane

There total 2 articles about 3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane 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: 68.0%

ethyl (2E)-3,7-dimethyl-6,7-epoxy-2-octen-1-yl carbonate (758692-14-7) + (4-(benzyloxy)phenyl)tri-n-butylstannane (145745-05-7) → 3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane (758692-17-0)

Guidance literature:

With water; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1021/jo049253r

Reference yield:

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol (40036-54-2) → 3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane (758692-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / tetrahydrofuran / 4 h / 20 °C

2: 68 percent / water / Pd(dba)2 / dimethylformamide / 48 h / 20 °C

With water; sodium hydride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Stille-type coupling;

DOI:10.1021/jo049253r

Reference yield: 48.0%

3-[(E)-5-(4-Benzyloxy-phenyl)-3-methyl-pent-3-enyl]-2,2-dimethyl-oxirane (758692-17-0) → (1S,3R)-3-(2-Benzyloxy-benzyl)-2,2-dimethyl-4-methylene-cyclohexanol

Guidance literature:

With 2,4,6-trimethyl-pyridine; manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/ejoc.200600389

upstream raw materials:

ethyl (2E)-3,7-dimethyl-6,7-epoxy-2-octen-1-yl carbonate

(4-(benzyloxy)phenyl)tri-n-butylstannane

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol