Ethyl 1-formylcyclobutanecarboxylate

Base Information

• Chemical Name: Ethyl 1-formylcyclobutanecarboxylate
• CAS No.: 57742-93-5
• Molecular Formula: C8H12 O3
• Molecular Weight: 156.181
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID60481311
• Wikidata: Q82316644
• Mol file: 57742-93-5.mol

Synonyms:57742-93-5;ETHYL 1-FORMYLCYCLOBUTANE-1-CARBOXYLATE;ETHYL 1-FORMYLCYCLOBUTANECARBOXYLATE;Cyclobutanecarboxylic acid, 1-formyl-, ethyl ester;1-formyl-cyclobutanecarboxylic acid ethyl ester;ETHYL1-FORMYLCYCLOBUTANE-1-CARBOXYLATE;SCHEMBL1606644;DTXSID60481311;HORWHQYLTMRHBX-UHFFFAOYSA-N;AKOS015904220;CS-0380567;EN300-195038;A831577;F2147-3074;Z1255492862

Chemical Property of Ethyl 1-formylcyclobutanecarboxylate

Chemical Property:

• Boiling Point: 206.2±23.0 °C(Predicted)
• PSA: 43.37000
• Density: 1.200±0.06 g/cm3(Predicted)
• LogP: 0.91870
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

ethyl1-formylcyclobutanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CCC1)C=O

Technology Process of Ethyl 1-formylcyclobutanecarboxylate

There total 3 articles about Ethyl 1-formylcyclobutanecarboxylate 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: 70.0%

ethyl 1-(hydroxymethyl)cyclobutanecarboxylate (1195-81-9) → ethyl 1-formylcyclobutanecarboxylate (57742-93-5)

Guidance literature:

With Dess-Martin periodane; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2008.12.114

Reference yield:

diethyl cyclobutane-1,1-dicarboxylate (3779-29-1) → ethyl 1-formylcyclobutanecarboxylate (57742-93-5)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; for 0.666667h; Cooling with acetone-dry ice;

Reference yield:

ethyl cyclobutylcarboxylate (14924-53-9) → ethyl 1-formylcyclobutanecarboxylate (57742-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

With oxalyl dichloride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-0029-1217703

upstream raw materials:

ethyl 1-(hydroxymethyl)cyclobutanecarboxylate

diethyl cyclobutane-1,1-dicarboxylate

ethyl cyclobutylcarboxylate

Downstream raw materials:

(1-ethenylcyclobutyl)diphenylmethanol

ethyl 4-(2-cyclobutylidenethyl)benzoate

N-{4-(1-ethoxycarbonylcyclobutyl)-4-hydroxy-2-butynyl}-N-(2-propynyl)-4-methylbenzenesulfonamide

N-{4-(1-ethoxycarbonylcyclobutyl)-2-phenylsulfonyl-2,3-butadienyl}-N-(2-propynyl)-4-methylbenzenesulfonamide

Refernces

• 1、 Iwasaki, Masayuki,Yorimitsu, Hideki,Oshima, Koichiro. "Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position". supporting information; experimental part. p. 2177 - 2179. Retrieved 2011/03/20.
• 2、 -. "Spiro derivatives as lipoxygenase inhibitors". Page/Page column 93. . Retrieved 2008/06/13.