Diethyl tetrahydrofurfurylmalonate

Base Information

• Chemical Name: Diethyl tetrahydrofurfurylmalonate
• CAS No.: 37136-39-3
• Molecular Formula: C12H20O5
• Molecular Weight: 244.288
• Hs Code.: 2932190090
• European Community (EC) Number: 253-357-1
• DSSTox Substance ID: DTXSID40958339
• Nikkaji Number: J260.741G
• Mol file: 37136-39-3.mol

Synonyms:37136-39-3;Diethyl tetrahydrofurfurylmalonate;diethyl 2-(oxolan-2-ylmethyl)propanedioate;EINECS 253-357-1;Diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate;diethyltetrahydrofurfurylmalonate;Diethyl Tetrahydrofufurylmalonate;SCHEMBL11531232;DTXSID40958339;diethyl (tetrahydrofurfuryl)malonate;AKOS015964851;Diethyl [(oxolan-2-yl)methyl]propanedioate;[[(Tetrahydrofuran)-2-yl]methyl]propanedioic acid diethyl ester;Propanedioic acid, ((tetrahydro-2-furanyl)methyl)-, diethyl ester

Chemical Property of Diethyl tetrahydrofurfurylmalonate

Chemical Property:

• Vapor Pressure: 0.000867mmHg at 25°C
• Refractive Index: 1.454
• Boiling Point: 304.6 °C at 760 mmHg
• Flash Point: 129.4 °C
• PSA: 61.83000
• Density: 1.091 g/cm³
• LogP: 1.29790
• Solubility.: DCM, Ethyl Acetate, Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 244.13107373
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

DiethylTetrahydrofurfurylmalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1CCCO1)C(=O)OCC
• Uses: Diethyl Tetrahydrofurfurylmalonate is an intermediate in synthesizing Nafronyl (N215000), which is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.

Technology Process of Diethyl tetrahydrofurfurylmalonate

There total 10 articles about Diethyl tetrahydrofurfurylmalonate 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: 88.0%

ethyl 2-carbethoxy-3-(2-furanyl)propenoate (17448-96-3) → diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate (37136-39-3)

Guidance literature:

With hydrogen; nickel; In ethanol; at 80 ℃; for 6h; under 56254.5 Torr;

Reference yield: 74.0%

tetrahydrofurfuryl bromide (1192-30-9) + diethyl malonate (105-53-3) → diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate (37136-39-3)

Guidance literature:

diethyl malonate; With sodium hydride; In N,N-dimethyl-formamide; toluene; at 20 ℃;

tetrahydrofurfuryl bromide; In N,N-dimethyl-formamide; toluene; at 95 ℃;

DOI:10.1021/ja053337f

Reference yield: 73.0%

n-Pent-4-enyl alcohol (821-09-0) + Diethyl 2-bromomalonate (685-87-0) → diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate (37136-39-3) + diethyl 2-(2-bromo-5-hydroxypentyl)malonate (1277180-99-0)

Guidance literature:

With Ir[(dF(CF₃)ppy)2(dtbbpy)]PF₆; lithium bromide; In water; N,N-dimethyl-formamide; for 12h; Visible-light irradiation; Inert atmosphere;

DOI:10.1021/ja108560e

upstream raw materials:

ethyl 2-carbethoxy-3-(2-furanyl)propenoate

tetrahydrofurfuryl bromide

diethyl malonate

sodium diethylmalonate

Downstream raw materials:

C₃₁H₃₈Br₂NO₅⁽¹⁺⁾*I^(1-)

bis(2-diethylaminoethyl) 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate

1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid

nafronyl

Refernces

• 1、 Coutant, Eloi P.,Hervin, Vincent,Gagnot, Glwadys,Ford, Candice,Baatallah, Racha,Janin, Yves L.. "Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate". supporting information. p. 2853 - 2860. Retrieved 2018/11/26.
• 2、 Jiao, Zhi-Wei,Zhang, Shu-Yu,He, Chuan,Tu, Yong-Qiang,Wang, Shao-Hua,Zhang, Fu-Min,Zhang, Yong-Qiang,Li, Hui. "Organocatalytic asymmetric direct Csp3 -H functionalization of ethers: A highly efficient approach to chiral spiroethers". supporting information; experimental part. p. 8811 - 8815. Retrieved 2012/10/08.