Diethyl 2-allyl-2-methylmalonate

Base Information

• Chemical Name: Diethyl 2-allyl-2-methylmalonate
• CAS No.: 53651-72-2
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.262
• European Community (EC) Number: 662-161-9
• Nikkaji Number: J1.087.740G
• Mol file: 53651-72-2.mol

Synonyms:53651-72-2;Diethyl 2-allyl-2-methylmalonate;2-Allyl-2-methylmalonic Acid Eiethyl Ester;diethyl 2-methyl-2-prop-2-enylpropanedioate;diethyl allyl(methyl)malonate;SCHEMBL3977030;Diethyl2-allyl-2-methylmalonate;CWGGTBZQRNZEEF-UHFFFAOYSA-N;Allylmethylmalonic acid diethyl ester;AKOS024339885;CS-T-01697;1,3-diethyl 2-methyl-2-(prop-2-en-1-yl)propanedioate

Chemical Property of Diethyl 2-allyl-2-methylmalonate

Chemical Property:

• Boiling Point: 89.7-90.5 °C(Press: 6.5-7 Torr)
• Density: 1.009±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 214.12050905
• Heavy Atom Count: 15
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

2-Allyl-2-methylmalonicAcidEiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(CC=C)C(=O)OCC
• Uses: 2-Allyl-2-MethylMalonic Acid Eiethyl Ester can be used in the preparation of Meprobamate (M227750) and its metabolites.

Technology Process of Diethyl 2-allyl-2-methylmalonate

There total 26 articles about Diethyl 2-allyl-2-methylmalonate 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: 100.0%

allyl bromide (106-95-6) + Diethyl methylmalonate (609-08-5) → diethyl allylmethylmalonate (53651-72-2)

Guidance literature:

Diethyl methylmalonate; With sodium ethanolate; In ethanol; for 0.333333h;

allyl bromide; In ethanol; for 12h;

DOI:10.1021/ol0700153

Reference yield: 100.0%

Allyl acetate (591-87-7) + Diethyl methylmalonate (609-08-5) → diethyl allylmethylmalonate (53651-72-2)

Guidance literature:

Diethyl methylmalonate; With sodium hydride; In tetrahydrofuran; at 25 ℃; for 0.5h;

Allyl acetate; With 1,4-di(diphenylphosphino)-butane; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at 55 ℃; for 3h; Further stages.;

DOI:10.1021/ol070707r

Reference yield: 98.0%

allyl alcohol (107-18-6) + Diethyl methylmalonate (609-08-5) → diethyl allylmethylmalonate (53651-72-2)

Guidance literature:

With 4-(9-borabicyclo[3.3.1]nonanyl)butyldiphenylphosphine; palladium diacetate; In 1,4-dioxane; for 1h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux;

DOI:10.1002/adsc.201800187

upstream raw materials:

sodium diethyl methylmalonate

allyl bromide

sodium diethyl methylmalonate

3-chloroprop-1-ene

Refernces

• 1、 Hegedus et al.. "". . p. 7747. Retrieved 1978.
• 2、 Fernandez Reina, Daniel,Ruffoni, Alessandro,Al-Faiyz, Yasair S. S.,Douglas, James J.,Sheikh, Nadeem S.,Leonori, Daniele. "Visible-Light-Mediated Reactions of Electrophilic Radicals with Vinyl and Allyl Trifluoroborates". . p. 4126 - 4130. Retrieved 2017/06/19.
• 3、 Xing, Xiangyou,O'Connor, Nicholas R.,Stoltz, Brian M.. "Palladium(II)-Catalyzed Allylic C H Oxidation of Hindered Substrates Featuring Tunable Selectivity Over Extent of Oxidation". supporting information. p. 11186 - 11190. Retrieved 2016/07/06.