Diethyl 2-ethenyl-2-methylpropanedioate

Base Information

• Chemical Name: Diethyl 2-ethenyl-2-methylpropanedioate
• CAS No.: 64770-16-7
• Molecular Formula: C10H16O4
• Molecular Weight: 200.235
• DSSTox Substance ID: DTXSID20504272
• Nikkaji Number: J1.062.337E
• Wikidata: Q82358642
• Mol file: 64770-16-7.mol

Synonyms:64770-16-7;diethyl 2-ethenyl-2-methylpropanedioate;Propanedioic acid, ethenylmethyl-, diethyl ester;1,3-DIETHYL 2-ETHENYL-2-METHYLPROPANEDIOATE;SCHEMBL2915795;diethyl 2-methyl-2-vinylmalonate;DTXSID20504272;Diethyl ethenyl(methyl)propanedioate

Chemical Property of Diethyl 2-ethenyl-2-methylpropanedioate

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C=C)C(=O)OCC

Technology Process of Diethyl 2-ethenyl-2-methylpropanedioate

There total 5 articles about Diethyl 2-ethenyl-2-methylpropanedioate 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%

ethene (74-85-1) + sodium diethyl methylmalonate (62116-54-5) → diethyl 2-ethyl-2-methylmalonate (2049-70-9) + ethyl 2-ethoxycarbonyl-2-methyl-3-butenoate (64770-16-7)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); triethylamine; In tetrahydrofuran; Product distribution; multistep reaction: 1.) -78 deg C, 2.) -60 deg C -> room temperature; palladium-assisted alkylation of various olefin with carbanions accompanied by reductive or β-elimination isolation procedure; stereo- and regioselectivity;

DOI:10.1021/ja00535a026

Reference yield: 84.0%

4-Iodobenzotrifluoride (455-13-0) + 2-[1-(hydroxy-dimethyl-silanyl)-vinyl]-2-methyl-malonic acid diethyl ester (818377-74-1) + 2-{1-[3-(2,2-Bis-ethoxycarbonyl-1-methylene-propyl)-1,1,3,3-tetramethyl-disiloxanyl]-vinyl}-2-methyl-malonic acid diethyl ester (818377-76-3) → ethyl 2-ethoxycarbonyl-2-methyl-3-butenoate (64770-16-7) + ethyl 2-ethoxycarbonyl-2-methyl-3-(4-trifluoromethylphenyl)-3-butenoate

Guidance literature:

With tetrabutyl ammonium fluoride; copper(l) chloride; bis(η3-allyl-μ-chloropalladium(II)); In N,N-dimethyl-formamide; at 45 ℃; for 40h;

DOI:10.1002/ejoc.200400339

Reference yield: 74.0%

1-iodo-2-methoxy-4-methylbenzene (186583-59-5) + 2-[1-(hydroxy-dimethyl-silanyl)-vinyl]-2-methyl-malonic acid diethyl ester (818377-74-1) + 2-{1-[3-(2,2-Bis-ethoxycarbonyl-1-methylene-propyl)-1,1,3,3-tetramethyl-disiloxanyl]-vinyl}-2-methyl-malonic acid diethyl ester (818377-76-3) → ethyl 2-ethoxycarbonyl-2-methyl-3-butenoate (64770-16-7) + ethyl (E)-2-ethoxycarbonyl-2-methyl-4-(4-methyl-2-methoxyphenyl)-3-butenoate + ethyl 2-ethoxycarbonyl-3-(2-methoxy-4-methylphenyl)-2-methyl-3-butenoate

Guidance literature:

With tetrabutyl ammonium fluoride; copper(l) chloride; bis(η3-allyl-μ-chloropalladium(II)); In N,N-dimethyl-formamide; at 45 ℃; for 40h;

DOI:10.1002/ejoc.200400339

upstream raw materials:

methyl magnesium iodide

diethyl isopropylidenemalonate

ethene

sodium diethyl methylmalonate