ETHYL 3-OXO-3-(FURAN-3-YL)PROPANOATE

Base Information

• Chemical Name: ETHYL 3-OXO-3-(FURAN-3-YL)PROPANOATE
• CAS No.: 36878-91-8
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29321900
• Mol file: 36878-91-8.mol

Synonyms:3-Furanpropionicacid, b-oxo-, ethyl ester (6CI);3-(Furan-3-yl)-3-oxopropanoic acid ethyl ester;3-(Furan-3-yl)-3-oxopropionicacid ethyl ester;Ethyl 3-(3-furyl)-3-oxopropanoate;Ethyl3-(3-furyl)-3-oxopropionate;Ethyl 3-furoylacetate;Ethyl3-oxo-3-(3-furanyl)propanoate;Ethyl 3-oxo-3-(3-furyl)propionate;NSC 350548;

Chemical Property of ETHYL 3-OXO-3-(FURAN-3-YL)PROPANOATE

Chemical Property:

• Appearance/Colour: clear colorless to orange liquid
• Vapor Pressure: 0.00791mmHg at 25°C
• Refractive Index: n20/D 1.489(lit.)
• Boiling Point: 268 °C at 760 mmHg
• Flash Point: 99.3 °C
• PSA: 56.51000
• Density: 1.162 g/cm³
• LogP: 1.41550
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl3-(Furan-3-yl)-3-oxopropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Uses: Ethyl β-oxo-3-furanpropionate has been used in the synthesis of deuterated 4-ipomeanol.

Technology Process of ETHYL 3-OXO-3-(FURAN-3-YL)PROPANOATE

There total 7 articles about ETHYL 3-OXO-3-(FURAN-3-YL)PROPANOATE 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: 91.0%

N-phenyl-N-tosylfuran-3-carboxamide + ethyl acetate (141-78-6) → Ethyl β-oxo-3-furanpropionate (36878-91-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 25 ℃; for 2h; chemoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.joc.0c02868

Reference yield: 68.0%

3-acetylfuran (14313-09-8) + Diethyl carbonate (105-58-8,76619-83-5) → Ethyl β-oxo-3-furanpropionate (36878-91-8)

Guidance literature:

With sodium hydride; In toluene; mineral oil; Reflux;

DOI:10.1021/acs.orglett.9b02012

Reference yield:

furan-3-carbonyl chloride (26214-65-3) + hydrogen ethyl malonate (1071-46-1) → Ethyl β-oxo-3-furanpropionate (36878-91-8)

Guidance literature:

hydrogen ethyl malonate; With [2,2]bipyridinyl; n-butyllithium; In tetrahydrofuran; hexane; at -70 - -10 ℃; Inert atmosphere;

furan-3-carbonyl chloride; In tetrahydrofuran; hexane; for 0.333333h; Inert atmosphere;

DOI:10.15227/orgsyn.061.0005

upstream raw materials:

furan-3-carbonyl chloride

ethyl acetoacetate

ethyl 3-furancarboxylate

ethyl acetate

Downstream raw materials:

3-(3-furyl)-1-(4-nitrophenyl)-1H-pyrazol-5-ol

(S)-4-ipomeanol

(R)-4-ipomeanol

ethyl 4-(3-(furan-3-yl)-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzoate

Refernces

• 1、 Xu, Kai,Zheng, Yan,Ye, Yong,Liu, Delong,Zhang, Wanbin. "Desymmetrization of meso-dicarbonatecyclohexene with β-Hydrazino carboxylic esters via a Pd-catalyzed allylic substitution cascade". supporting information. p. 8836 - 8841. Retrieved 2020/11/30.
• 2、 Son, Jeong-Yu,Kim, Jonghye,Han, Sang Hoon,Kim, Sung Hong,Lee, Phil Ho. "Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes". supporting information. p. 5408 - 5411. Retrieved 2016/11/06.