Ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate

Base Information

• Chemical Name: Ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate
• CAS No.: 3511-34-0
• Molecular Formula: C8H10O4
• Molecular Weight: 170.165
• European Community (EC) Number: 965-102-8
• DSSTox Substance ID: DTXSID80485194
• Wikidata: Q82324167
• Mol file: 3511-34-0.mol

Synonyms:ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate;3511-34-0;ethyl 2-methyl-4-oxofuran-3-carboxylate;MFCD06251769;ST51035772;SCHEMBL18605429;DTXSID80485194;AKOS024385178;NS-01380;SY200365;CS-0109726;EN300-206794;ethyl2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate

Chemical Property of Ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 252

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(OCC1=O)C
• General Description: **3-Furancarboxylic acid, 4,5-dihydro-2-methyl-4-oxo-, ethyl ester** is a 2-substituted 4,5-dihydro-4-oxo-3-furancarboxylate derivative synthesized via an acylative intramolecular cyclization of sulfonium salts. This method involves forming a mixed anhydride with trifluoroacetic anhydride and N-methylimidazole, followed by in situ generation of a reactive acylammonium intermediate, enabling efficient access to such furan carboxylates. 3-Furancarboxylic acid, 4,5-dihydro-2-methyl-4-oxo-, ethyl ester is part of a broader class of synthetically accessible derivatives with potential applications in organic and medicinal chemistry. (Other names for 3-Furancarboxylic acid, 4,5-dihydro-2-methyl-4-oxo-, ethyl ester may include ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate or similar systematic variants.)

Technology Process of Ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate

There total 5 articles about Ethyl 2-methyl-4-oxo-4,5-dihydrofuran-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: 56.0%

3-ethoxycarbonyl-2-oxopropyldiphenylsulfonium tetrafluoroborate + acetic anhydride (108-24-7) → ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate (3511-34-0)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.11.035

Reference yield: 44.0%

ethyl acetoacetate (141-97-9) + chloroacetyl chloride (79-04-9) → ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate (3511-34-0)

Guidance literature:

ethyl acetoacetate; With magnesium ethylate; In ethanol; benzene; at 23 ℃; for 1.5h; Inert atmosphere;

chloroacetyl chloride; In ethanol; acetonitrile; benzene; at 0 - 23 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.201712065

Reference yield: 27.0%

N-acetoxysuccinimide (14464-29-0,57212-69-8) + 3-ethoxycarbonyl-2-oxopropyldiphenylsulfonium tetrafluoroborate → ethyl 2-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate (3511-34-0) + 5-ethoxy-3(2H)-furanone

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.11.035

upstream raw materials:

ethyl acetoacetate

chloroacetyl chloride

N-acetoxysuccinimide

acetyl chloride

Downstream raw materials:

2-Methyl-4-oxo-5-[1-p-tolyl-meth-(Z)-ylidene]-4,5-dihydro-furan-3-carboxylic acid ethyl ester

4-Oxo-5-[1-p-tolyl-meth-(Z)-ylidene]-2-((E)-2-p-tolyl-vinyl)-4,5-dihydro-furan-3-carboxylic acid ethyl ester

5-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2-methyl-4-oxo-4,5-dihydro-furan-3-carboxylic acid ethyl ester

5-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2-[(E)-2-(3-chloro-phenyl)-vinyl]-4-oxo-4,5-dihydro-furan-3-carboxylic acid ethyl ester

Refernces

Reactivity of 5-Methyl-3(2H)-furanones toward Schiff Bases; Synthesis of 5-Styryl-3(2H)-furanone Derivatives

10.1055/s-1981-29328

The research investigates the reactivity of 5-methyl-3(2H)-furanones towards Schiff bases, aiming to synthesize 5-styryl-3(2H)-furanone derivatives. The study demonstrates that the reaction of Schiff bases with ketones, which is formally analogous to the aldol reaction, is feasible under acidic conditions. Key chemicals used include 4-ethoxycarbonyl-5-methyl-3-oxo-2,3-dihydrofuran (1), various imines (2), and acetic acid. The researchers found that the reaction proceeds stereospecifically to form (Z)-2-benzylidene-4-ethoxycarbonyl-3-oxo-5-(E)-styryl-2,3-dihydrofurans (3) when two mol equivalents of imines are used. For compounds with different aryl groups, an intermediate (4) is first prepared and then reacted with a second Schiff base. The study concludes that the 5-methyl-3(2H)-furanone system exhibits high reactivity, and the synthesized compounds' structures are confirmed by microanalyses and spectral data.

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