Methyl 4-oxotetrahydrofuran-3-carboxylate

Base Information

• Chemical Name: Methyl 4-oxotetrahydrofuran-3-carboxylate
• CAS No.: 57595-23-0
• Molecular Formula: C6H8O4
• Molecular Weight: 144.127
• Hs Code.: 2932190090
• European Community (EC) Number: 855-932-8
• DSSTox Substance ID: DTXSID50562789
• Nikkaji Number: J2.580.718I
• Mol file: 57595-23-0.mol

Synonyms:Methyl 4-oxotetrahydrofuran-3-carboxylate;57595-23-0;METHYL 4-OXOOXOLANE-3-CARBOXYLATE;MFCD19707049;Tetrahydro-4-oxo-3-furancarboxylic Acid Methyl Ester;3-Furancarboxylic acid, tetrahydro-4-oxo-, methyl ester;SCHEMBL1566094;DTXSID50562789;FCUDJBUBWCJOLK-UHFFFAOYSA-N;4-carbomethoxytetrahydro-3-furanone;AMY11820;CS-D0559;AKOS005266433;AKOS016842995;PB18290;Methyl4-oxotetrahydrofuran-3-carboxylate;DS-16817;SY014732;methyl tetrahydro-4-oxofuran-3-carboxylate;EN300-95806;A831514;4-oxo-tetrahydrofuran-3-carboxylic acid methyl ester;tetrahydrofuran-3-one-4-carboxylic acid-methyl ester;4-oxo-tetrahydro furane 3-carboxylic acid methyl ester;4-oxo-tetrahydro-furan-3-carboxylic acid methyl ester

Chemical Property of Methyl 4-oxotetrahydrofuran-3-carboxylate

Chemical Property:

• Boiling Point: 220℃
• PKA: 10.72±0.20(Predicted)
• Flash Point: 91℃
• PSA: 52.60000
• Density: 1.265
• LogP: -0.62510
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 163

Purity/Quality:

NLT 98% ^*data from raw suppliers

Tetrahydro-4-oxo-3-furancarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1COCC1=O
• Uses: Tetrahydro-4-oxo-3-furancarboxylic Acid Methyl Ester, is used for the preparation of fused-pyrimidine derivatives as a series of novel GPR119 agonists.

Technology Process of Methyl 4-oxotetrahydrofuran-3-carboxylate

There total 6 articles about Methyl 4-oxotetrahydrofuran-3-carboxylate 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: 82.5%

glycolic acid methyl ester (96-35-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-oxotetrahydrofuran-3-carboxylate (57595-23-0)

Guidance literature:

glycolic acid methyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.1h;

acrylic acid methyl ester; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; for 4h;

Reference yield: 80.7%

ethyl 2-hydroxyacetate (623-50-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-oxotetrahydrofuran-3-carboxylate (57595-23-0)

Guidance literature:

ethyl 2-hydroxyacetate; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.1h;

acrylic acid methyl ester; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; for 4h; Solvent;

Reference yield: 54.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-oxotetrahydrofuran-3-carboxylate (57595-23-0)

Guidance literature:

glycolic acid methyl ester; With sodium hydride; In diethyl ether;

acrylic acid methyl ester; In dimethyl sulfoxide; at 0 - 20 ℃;

With hydrogenchloride; In water; dimethyl sulfoxide;

upstream raw materials:

glycolic acid methyl ester

acrylic acid methyl ester

ethyl 2-hydroxyacetate

(±)-(tetrahydrofuran-3-yl)hydrazine hydrochloride

Downstream raw materials:

methyl 4-(phenylamino)-2,5-dihydrofuran-3-carboxylate

5,7-dihydrofuro[3,4-d]pyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 -. "ISOXAZOLE CARBOXYLIC ACIDS AS LPA ANTAGONISTS". Page/Page column 96-97. . Retrieved 2021/01/22.
• 2、 Harvey, Andrew J.,Avery, Thomas D.,Schaeffer, Laurent,Joseph, Christophe,Huff, Belinda C.,Singh, Rajinder,Morice, Christophe,Giethlen, Bruno,Grishin, Anton A.,Coles, Carolyn J.,Kolesik, Peter,Wagner, Stéphanie,Andriambeloson, Emile,Huyard, Bertrand,Poiraud, Etienne,Paul, Dharam,O'Connor, Susan M.. "Discovery of BNC375, a Potent, Selective, and Orally Available Type i Positive Allosteric Modulator of α7 nAChRs". supporting information. p. 754 - 760. Retrieved 2019/04/17.