2-Pentenoic acid, 3,4,4-trimethyl-, ethyl ester

Base Information

• Chemical Name: 2-Pentenoic acid, 3,4,4-trimethyl-, ethyl ester
• CAS No.: 91140-23-7
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• Mol file: 91140-23-7.mol

Synonyms:

Chemical Property of 2-Pentenoic acid, 3,4,4-trimethyl-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Pentenoic acid, 3,4,4-trimethyl-, ethyl ester

There total 10 articles about 2-Pentenoic acid, 3,4,4-trimethyl-, 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: 71.0%

3,3-dimethyl-butan-2-one (75-97-8) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → (E)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester (21016-48-8,91140-23-7,16812-82-1)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.583333h; Inert atmosphere;

3,3-dimethyl-butan-2-one; In tetrahydrofuran; mineral oil; Inert atmosphere; Reflux;

DOI:10.1002/chem.201101524

Reference yield: 47.0%

3,3-dimethyl-butan-2-one (75-97-8) + triethyl phosphonoformate (1474-78-8) → (E)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester (21016-48-8,91140-23-7,16812-82-1)

Guidance literature:

triethyl phosphonoformate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1.25h; Inert atmosphere;

3,3-dimethyl-butan-2-one; In tetrahydrofuran; for 20h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201303915

Reference yield:

3,3-dimethyl-butan-2-one (75-97-8) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → (E)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester (21016-48-8,91140-23-7,16812-82-1) + (Z)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester (21016-48-8)

Guidance literature:

In 1,2-dimethoxyethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja962631s

upstream raw materials:

3,3-dimethyl-butan-2-one

diethoxyphosphoryl-acetic acid ethyl ester

carbethoxymethyldibutyltelluronium bromide

3-Acetoxy-3,4,4-trimethyl-pentanoic acid ethyl ester

Downstream raw materials:

ethyl 4,4-dimethyl-3-methylenepentanoate

(E)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester

Z-ethyl-3,4-dimethyl-2-pentenoate

ethyl 2-(1',2',2'-trimethylcyclopropyl)acetate

Refernces

• 1、 Xu, Lijun,Liu, Zhubo,Dong, Weipeng,Song, Jinyu,Miao, Maozhong,Xu, Jianfeng,Ren, Hongjun. "Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents". supporting information. p. 6333 - 6337. Retrieved 2015/06/08.
• 2、 Bernasconi, Maurizio,Ramella, Vincenzo,Tosatti, Paolo,Pfaltz, Andreas. "Iridium-catalyzed asymmetric hydrogenation of 3,3-disubstituted allylic alcohols in ethereal solvents". supporting information. p. 2440 - 2444. Retrieved 2014/03/21.