4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester

Base Information

• Chemical Name: 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester
• CAS No.: 107408-54-8
• Molecular Formula: C₂₉H₂₉O₃P
• Molecular Weight: 456.521

Synonyms:4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester

Chemical Property of 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester

Chemical Property:

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Technology Process of 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester

There total 4 articles about 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester 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: 87.0%

ethyl 9-iodo-3-oxo-2-(triphenylphosphoranylidene)-4-(E),8(Z)-nonadienoate (107408-22-0) → 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester (107408-54-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

Reference yield: 61.0%

4-Bromo-4-cyclopentyl-3-oxo-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester → 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester (107408-54-8)

Guidance literature:

With triphenylphosphine; In ethanol; for 1h; Heating;

Reference yield:

5,5-dimethoxy-1-iodo-1(Z)-pentene (107408-20-8) → 4-Cyclopent-2-enyl-3-oxo-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester (107408-54-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / 50percent aq. HOAc / 14 h

2: NaH, EtOH / tetrahydrofuran / 0.75 h

3: 1.) t-BuLi / 1.) THF, pentane, -78 deg C, 40 min, 2.) THF, pentane, 55 deg C, 1 h

4: 61 percent / Ph₃P / ethanol / 1 h / Heating

With ethanol; tert.-butyl lithium; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; ethanol;

upstream raw materials:

ethyl 9-iodo-3-oxo-2-(triphenylphosphoranylidene)-4-(E),8(Z)-nonadienoate

5,5-dimethoxy-1-iodo-1(Z)-pentene

(Z)-5-iodo-4-pentenal

Downstream raw materials:

4-Cyclopentyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester

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