benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate

Base Information

• Chemical Name: benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate
• CAS No.: 158604-58-1
• Molecular Formula: C₁₄H₁₄O₃
• Molecular Weight: 230.263
• Mol file: 158604-58-1.mol

Synonyms:benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate

Chemical Property of benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate

There total 5 articles about benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate 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: 91.0%

2-(4-oxocyclopent-2-en-1-yl)acetic acid (74877-21-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate (158604-58-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1002/hlca.19940770214

Reference yield:

(1R*,2S*,3S*,5R*)-(±)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one (56011-39-3,71963-06-9,73346-97-1,73346-98-2,74524-00-8,89195-25-5) → benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate (158604-58-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dihydrogen peroxide; acetic acid / dichloromethane / 20 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 80 °C / Inert atmosphere

3.1: dimethyl sulfoxide; trifluoroacetic anhydride / dichloromethane / 0.83 h / -60 °C / Inert atmosphere

3.2: 1.5 h / -60 - 20 °C / Inert atmosphere

3.3: 20 °C / Inert atmosphere

4.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2011.12.013

Reference yield:

(3aR*,4S*,5S*,6aR*)-(±)-4-bromo-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one → benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate (158604-58-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 80 °C / Inert atmosphere

2.1: dimethyl sulfoxide; trifluoroacetic anhydride / dichloromethane / 0.83 h / -60 °C / Inert atmosphere

2.2: 1.5 h / -60 - 20 °C / Inert atmosphere

2.3: 20 °C / Inert atmosphere

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2011.12.013

upstream raw materials:

2-(4-oxocyclopent-2-en-1-yl)acetic acid

benzyl alcohol

bicyclo[3.2.0]hept-2-en-6-one

(1R*,2S*,3S*,5R*)-(±)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one

Downstream raw materials:

benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate