dimethyl 2-(2-chlorobenzylidene)propanedioate

Base Information

• Chemical Name: dimethyl 2-(2-chlorobenzylidene)propanedioate
• CAS No.: 59832-47-2
• Molecular Formula: C₁₂H₁₁ClO₄
• Molecular Weight: 254.67
• Mol file: 59832-47-2.mol

Synonyms:dimethyl 2-(2-chlorobenzylidene)propanedioate

Chemical Property of dimethyl 2-(2-chlorobenzylidene)propanedioate

Chemical Property:

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Technology Process of dimethyl 2-(2-chlorobenzylidene)propanedioate

There total 1 articles about dimethyl 2-(2-chlorobenzylidene)propanedioate 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: 95.0%

2-chloro-benzaldehyde (89-98-5) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-(2-chlorobenzylidene)propanedioate (59832-47-2)

Guidance literature:

With indium(III) chloride; acetic anhydride; In toluene; at 60 ℃; for 8h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.5b00011

Reference yield: 92.0%

indole (120-72-9) + dimethyl 2-(2-chlorobenzylidene)propanedioate (59832-47-2) → dimethyl 2-[(2-chlorophenyl)(1H-indol-3-yl)methyl]malonate

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at -40 ℃; for 18h;

DOI:10.1055/s-0036-1589068

Reference yield: 90.0%

C13H18OSi (1030919-27-7) + dimethyl 2-(2-chlorobenzylidene)propanedioate (59832-47-2) → dimethyl 2-((Z)-2-benzylidene-1-(2-chlorophenyl)-3-oxobutyl)propanedioate (1030919-37-9)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; scandium tris(trifluoromethanesulfonate); In acetonitrile; at -20 ℃; regioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol800745q

upstream raw materials:

2-chloro-benzaldehyde

malonic acid dimethyl ester

Downstream raw materials:

dimethyl 2-((Z)-2-benzylidene-1-(2-chlorophenyl)-3-oxobutyl)propanedioate

dimethyl 2-(2-chlorophenyl)cyclopropane-1,1-dicarboxylate

Refernces

• 1、 Borisov, Denis D.,Chermashentsev, Grigorii R.,Novikov, Roman A.,Tomilov, Yury V.. "Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates". supporting information. p. 2253 - 2259. Retrieved 2021/03/04.
• 2、 Zhang, Jiantao,Jiang, Huanfeng,Zhu, Shifa. "Cascade One-Pot Synthesis of Indanone-Fused Cyclopentanes from the Reaction of Donor-Acceptor Cyclopropanes and Enynals via a Sequential Hydrolysis/Knoevenagel Condensation/[3+2] Cycloaddition". supporting information. p. 2924 - 2930. Retrieved 2017/09/08.