(E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate

Base Information

• Chemical Name: (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate
• CAS No.: 894421-52-4
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 894421-52-4.mol

Synonyms:(E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate

Chemical Property of (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate

There total 8 articles about (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate 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: 88.0%

ethyl (E)-crotonate (623-70-1) + 3-cyclopentyloxy-4-methoxyphenylboronic acid (159613-21-5) → (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate (894421-52-4)

Guidance literature:

With oxygen; sodium carbonate; palladium diacetate; In N,N-dimethyl-formamide; at 50 ℃; for 12h; under 760 Torr;

DOI:10.1016/j.tet.2006.03.017

Reference yield:

5-bromo-2-methoxyphenol (37942-01-1) → (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate (894421-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / K₂CO₃ / dimethylformamide / 12 h / 50 °C

2.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C

2.2: diethyl ether; hexane / 1 h / -78 °C

3.1: 88 percent / Na₂CO₃; O₂ / Pd(OAc)2 / dimethylformamide / 12 h / 50 °C / 760 Torr

With n-butyllithium; oxygen; sodium carbonate; potassium carbonate; palladium diacetate; In diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.03.017

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 1-[3-(cyclopentyloxy)-4-methoxyphenyl]-ethanone (141184-48-7) → (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate (894421-52-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

DOI:10.1021/ol702193v

upstream raw materials:

ethyl (E)-crotonate

3-cyclopentyloxy-4-methoxyphenylboronic acid

diethoxyphosphoryl-acetic acid ethyl ester

1-[3-(cyclopentyloxy)-4-methoxyphenyl]-ethanone

Downstream raw materials:

(S)-rolipram

(R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one

(Z)-ethyl 4-azido-3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate

(Z)-ethyl 4-bromo-3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate