(R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate

Base Information

• Chemical Name: (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate
• CAS No.: 1399841-17-8
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 1399841-17-8.mol

Synonyms:

Chemical Property of (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate

There total 4 articles about (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate 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:

(E)-ethyl 2-(4-methoxybenzoyl)-6-oxohex-4-enoate (1399841-35-0) → (S)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate + (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate (1399841-17-8)

Guidance literature:

With (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; In dichloromethane; at 23 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201203382

Reference yield:

C16H18O5 → (S)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate + (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate (1399841-17-8)

Guidance literature:

With (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; In 1,2-dichloro-ethane; at 23 ℃; Overall yield = 71 %; Inert atmosphere;

DOI:10.1039/c4cc09308a

Reference yield:

(E)-ethyl 2-(4-methoxybenzoyl)-6-hydroxyhex-4-enoate (1399840-81-3) → (S)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate + (R)-ethyl 2-(4-methoxyphenyl)cyclopent-2-enecarboxylate (1399841-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium chlorochromate / dichloromethane / 2 h / 23 °C / Inert atmosphere

2: (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate / dichloromethane / 12 h / 23 °C / Inert atmosphere

With (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; pyridinium chlorochromate; In dichloromethane;

DOI:10.1002/anie.201203382

upstream raw materials:

(E)-ethyl 2-(4-methoxybenzoyl)-6-hydroxyhex-4-enoate

(E)-ethyl 2-(4-methoxybenzoyl)-6-oxohex-4-enoate

ethyl 4-methoxybenzoylacetate