T-butyl-3-oxocyclobutanecarboxylate Chemical Properties

Boiling point:

230.4±33.0 °C(Predicted)

Density 

1.1g/ml

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

semi-solid

color 

Colourless

InChI

InChI=1S/C9H14O3/c1-9(2,3)12-8(11)6-4-7(10)5-6/h6H,4-5H2,1-3H3

InChIKey

JINYZTGTQXDUQR-UHFFFAOYSA-N

SMILES

C1(C(OC(C)(C)C)=O)CC(=O)C1

Safety Information

HS Code 

2918300090

T-butyl-3-oxocyclobutanecarboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 3-oxocyclobutanecarboxylate from 3-oxocyclobutanecarboxylic acid and tert-butanol: To a solution of commercially available 3-oxocyclobutanecarboxylic acid (11.4 g, 100 mmol) in anhydrous dichloromethane (DCM, 100 mL) was added N,N'-dicyclohexylcarbodiimide (DCC, 31 g, 150 mmol) and tert-butanol (8.9 g, 120 mmol). 120 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction was quenched with deionized water and the aqueous phase was extracted with DCM. The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the target product tert-butyl 3-oxocyclobutanecarboxylate (15.1 g, 89% yield).

References

[1] Patent: WO2014/131855, 2014, A1. Location in patent: Page/Page column 77
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
[3] Journal of Organic Chemistry, 1993, vol. 58, # 1, p. 100 - 110
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 627 - 640
[5] Patent: US2009/298894, 2009, A1. Location in patent: Page/Page column 44

T-butyl-3-oxocyclobutanecarboxylate(145549-76-4)Related Product Information

• (3-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER
• Methyl 3-hydroxycyclobuta...
• METHYL 3-OXOCYCLOBUTANECARBOXYLATE
• BENZYL 3-OXOCYCLOBUTYLCARBAMATE
• 3-Hydroxy-cyclobutanecarboxylic acid ethyl ester
• 3-HYDROXYCYCLOBUTANECARBOXYLIC ACID
• tert-butyl 3-hydroxycyclobutanecarboxylate
• Cyclobutanecarboxylic acid, 3-methylene-, methyl ester (6CI,8CI,9CI)
• Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI)
• ETHYL 3-OXO CYCLOBUATNE CARBOXYLATE
• 3-Oxocyclobutanecarboxylic acid