Ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

Base Information

• Chemical Name: Ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate
• CAS No.: 3385-34-0
• Molecular Formula: C10H12 O4
• Molecular Weight: 196.203
• Hs Code.: 29322090
• European Community (EC) Number: 222-195-3
• NSC Number: 602920,18911
• UNII: Z83SZN6YKC
• DSSTox Substance ID: DTXSID80187489
• Nikkaji Number: J24.829K
• Wikidata: Q72475594
• ChEMBL ID: CHEMBL1579791
• Mol file: 3385-34-0.mol

Synonyms:ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate;ethyl isodehydracetate;ethyl isodehydroacetate;ethylisodehydroacetate

Chemical Property of Ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

Chemical Property:

• Appearance/Colour: Colorless or pale yellow liquid
• Vapor Pressure: 0.00153mmHg at 25°C
• Melting Point: 17-18 ºC
• Refractive Index: n20/D 1.515(lit.)
• Boiling Point: 290-295 ºC
• Flash Point: 145.8 °C
• PSA: 56.51000
• Density: 1.167
• LogP: 1.43330
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• Water Solubility.: Insoluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 336

Purity/Quality:

99% ^*data from raw suppliers

EthylIsodehydroacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(OC(=O)C=C1C)C
• Uses: Ethyl isodehydroacetate is used in the synthesis of bidentate ligands. Also used in the preparation of insect growth regulators with juvenile hormone activity. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of Ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

There total 12 articles about Ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-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: 80.0%

ethyl acetoacetate (141-97-9) → ethyl isodehydroacetate (3385-34-0)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; for 48h;

Reference yield: 65.0%

ethyl 2,3-butadienoate (14369-81-4) + ethyl acetoacetate (141-97-9) → ethyl isodehydroacetate (3385-34-0)

Guidance literature:

With potassium carbonate; In acetone; for 72h; Heating;

DOI:10.1055/s-2006-942493

Reference yield: 40.0%

ethyl acetoacetate (141-97-9) + malonoyl dichloride (1663-67-8) → ethyl 4-hydroxy-6-methyl-2-oxo-2H-pyran-5-carboxylate (66533-46-8) + ethyl isodehydroacetate (3385-34-0)

Guidance literature:

In benzene; Heating;

DOI:10.1016/S0040-4039(00)99205-0

upstream raw materials:

ethyl acetoacetate

sodium ethyl acetylacetate enolate

E-Ethyl β-chlorocrotonate

benzene

Downstream raw materials:

optically inactive N,N'-bis-(1-methyl-2-phenyl-ethyl)-urea

3-methyl-4-((E)-veratrylidene)-cis-pentenedioic acid

1,3-bis[2-(3,4-dimethoxyphenyl)ethyl]urea

1,3-dibenzylurea

Refernces

• 1、 Huang, Xian,Shen, Ruwei. "Poly substituted 5-functionalized 2-pyrone derivatives: Facile synthesis via tandem nucleophilic addition/lactonization reaction of 1,2-allenyl esters". . p. 2731 - 2737. Retrieved 2006.
• 2、 Al-Majid, Abdullah M. A.,Al-Othman, Zeid A.,Islam, Mohammad Shahidul. "Synthesis of some C2-symmetric bidentate ligands and their complexes derived from Feist's acid". experimental part. p. 268 - 277. Retrieved 2012/04/10.