ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate

Base Information

• Chemical Name: ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• CAS No.: 1802-02-4
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• Mol file: 1802-02-4.mol

Synonyms:

Chemical Property of ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate

Chemical Property:

• Vapor Pressure: 0.0372mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate

There total 45 articles about ethyl (3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate 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: 93.0%

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate (97-41-6) → ethyl trans-(+/-)-chrysanthemate (97-41-6,1802-02-4,7377-84-6,15543-65-4,16642-27-6,34909-55-2,41641-25-2,41641-26-3,41641-27-4)

Guidance literature:

With sodium hydride; In mineral oil; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02767

Reference yield: 92.63%

2,5-Dimethyl-2,4-hexadiene (764-13-6) + 1-acetoxy-2-aminoethane hydrochloride (20739-39-3) → ethyl trans-(+/-)-chrysanthemate (97-41-6,1802-02-4,7377-84-6,15543-65-4,16642-27-6,34909-55-2,41641-25-2,41641-26-3,41641-27-4)

Guidance literature:

1-acetoxy-2-aminoethane hydrochloride; With sodium nitrite; In water; 1,2-dichloro-ethane; at -2 - 2 ℃;

2,5-Dimethyl-2,4-hexadiene; With 2,6-di-tert-butyl-4-methyl-phenol; copper(l) chloride; In 1,2-dichloro-ethane; at 55 - 60 ℃;

Reference yield: 65.0%

2,2-dibromopropane (594-16-1) + ethyl (E)-5-methyl-2,4-hexadienoate (54542-32-4) → ethyl trans-(+/-)-chrysanthemate (97-41-6,1802-02-4,7377-84-6,15543-65-4,16642-27-6,34909-55-2,41641-25-2,41641-26-3,41641-27-4)

Guidance literature:

ethyl (E)-5-methyl-2,4-hexadienoate; With C₂₉H₃₅Br₂CoN₃; zinc dibromide; zinc; In tetrahydrofuran; at 22 ℃; for 0.25h; Inert atmosphere; Glovebox;

2,2-dibromopropane; In tetrahydrofuran; at 22 ℃; for 24h; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201807542

upstream raw materials:

ethanol

trans-chrysanthemic acid

pyrocin

ethyl 3-methylbut-2-enoate

Downstream raw materials:

ethyl trans-(+/-)-chrysanthemate

trans-chrysanthemic acid

(1S,3S)-trans-chrysanthemic acid

(S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate

Refernces

• 1、 Cho, Yong Hyun,Kim, Jae Hyung,An, Hyeju,Ahn, Kwang-Hyun,Kang, Eun Joo. "Cycloaddition Reactions of Alkene Radical Cations using Iron(III)-Phenanthroline Complex". supporting information. p. 2183 - 2188. Retrieved 2020/04/29.
• 2、 Werth, Jacob,Uyeda, Christopher. "Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes". supporting information. p. 13902 - 13906. Retrieved 2018/10/02.