3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER Chemical Properties

Boiling point:

91-94 °C(Press: 1.8 Torr)

Density 

1.065±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.51±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

HS Code 

2918999090

3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER Usage And Synthesis

Uses

Ethyl 3-cyclopentyl-3-oxopropionate can be used as a pharmaceutical synthesis intermediate.

Synthesis

6a) A hexane solution of 2.4 M n-butyllithium (92.0 mL, 230 mmol) was slowly added dropwise to a solution containing monoethyl malonate (13.6 mL, 115 mmol) and a catalytic amount of 2,2'-bipyridine at -55 to -65 °C. After the dropwise addition, cyclopentanecarbonyl chloride (7.0 mL, 58 mmol) was added in batches. The reaction mixture was gradually warmed to room temperature with stirring and subsequently poured into a mixture of 1N aqueous hydrochloric acid solution and ether. The organic layer was separated, washed three times with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, concentrated and then purified by silica gel column chromatography (eluent: 0-5% ethyl acetate in hexane solution with gradient elution) to afford ethyl 3-cyclopentyl-3-oxopropanoate (9.50 g, 89% yield).1H-NMR (400 MHz, DMSO-d6) δ 4.06 (q, J = 7 Hz. 2H), 3.60 (s, 2H), 2.99-2.91 (m, 1H), 1.78-1.47 (m, 8H), 1.15 (t, J = 7 Hz, 3H).

References

[1] Patent: US2008/96921, 2008, A1. Location in patent: Page/Page column 42
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 17, p. 3186 - 3201

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