24922-00-7

Basic information

• Product Name: 3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER
• Synonyms: ETHYL 3-CYCLOPENTYL-3-OXOPROPANOATE;3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER;Ethyl 3-cyclopentyl-3-oxopropionate;Cyclopentanepropanoicacid, b-oxo-, ethyl ester
• CAS NO: 24922-00-7
• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.23
• Mol File: 24922-00-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 255.3 °C at 760 mmHg
• Flash Point: 106.1 °C
• Appearance: /
• Density: 1.065 g/cm³
• Vapor Pressure: 0.0165mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.51±0.20(Predicted)
• CAS DataBase Reference: 3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER(24922-00-7)
• EPA Substance Registry System: 3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER(24922-00-7)

Safety Data

• Hazardous Substances Data: 24922-00-7(Hazardous Substances Data)

Usage

General Description

3-Cyclopentyl-3-oxo-propionic acid ethyl ester is a chemical compound with the molecular formula C9H14O3. It is an ester formed from the condensation of cyclopentylacetic acid and ethanol, and is commonly used as a pharmaceutical intermediate in the synthesis of various drugs. The compound is known for its strong odor and is classified as a flammable liquid. It is also used in the production of fragrances and flavors due to its characteristic aroma. Additionally, it has been studied for its potential applications in the field of organic chemistry and drug development.

InChI:InChI=1/C10H16O3/c1-2-13-10(12)7-9(11)8-5-3-4-6-8/h8H,2-7H2,1H3

Synthetic route

6-bicyclo<3.1.0>hexan-6-ol (71911-64-3) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
In neat (no solvent) at 110℃;	99%

3-cyclopentyl-2-diazo-3-hydroxy-propionic acid ethyl ester (811467-21-7) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
With copper(II) sulfate at 20℃; for 3h;	91%

Cyclopentanecarboxylic acid chloride (4524-93-0) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
Stage #1: hydrogen ethyl malonate With [2,2]bipyridinyl; n-butyllithium In hexanes at -65 - -55℃; Stage #2: Cyclopentanecarboxylic acid chloride In hexanes at 20℃;	89%
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 2 h / 0 - 20 °C 2: toluene / 24 h / 80 °C View Scheme

Cyclopentanecarboxylic acid chloride (4524-93-0) + ethyl potassium malonate (6148-64-7) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
With triethylamine; magnesium chloride In acetonitrile at 0℃; for 4h;	77%

6-bicyclo<3.1.0>hexan-6-ol (71911-61-0) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
at 300℃; for 1h;	52%

2-cyclopentanecarbonyl-3-oxo-butyric acid ethyl ester (412018-99-6) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
With diethyl ether; ammonia

1-cyclopentylethanone (6004-60-0) + Diethyl carbonate (105-58-8) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
With sodium amide

ethanol (64-17-5) + 5-(cyclopentanecarbonyl)2,2-dimethyl-1,3-dioxane-4,6-dione (134302-12-8) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
In toluene at 80℃; for 24h; Yield given;

diethyl malonate (105-53-3) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) Na / 1. benzene, reflux, 8 h; 2. 2h at 0 deg C, then 6 h room temp. 2: 52 percent / 1 h / 300 °C View Scheme

Cyclopentanecarboxylic acid chloride (4524-93-0) + ethyl acetate (141-78-6) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7)

Conditions	Yield
Stage #1: ethyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: Cyclopentanecarboxylic acid chloride In tetrahydrofuran; hexane at -78℃; for 0.0833333h;

Cyclopentanecarboxylic acid chloride (4524-93-0) + ethyl acetate (141-78-6) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + C10H16O3

Conditions	Yield
Stage #1: ethyl acetate With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.25h; Stage #2: Cyclopentanecarboxylic acid chloride In tetrahydrofuran at -78℃; for 2h; Overall yield = 643 mg;

cyclopentanecarboxylic acid (3400-45-1) → ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + C10H16O3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C 2.2: 2 h / -78 °C View Scheme

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + guanidine hydrochloride (50-01-1) → 2-amino-6-cyclopentyl-4-hydroxypyrimidine

Conditions	Yield
With potassium tert-butylate In methanol at 23 - 60℃;	88%

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + guanidine hydrochloride (50-01-1) → 2-amino-6-cyclopentyl-3H-pyrimidin-4-one (199863-76-8)

Conditions	Yield
Stage #1: ethyl 3-cyclopentyl-3-oxopropionate; guanidine hydrochloride With potassium tert-butylate In methanol at 20 - 60℃; Stage #2: With hydrogenchloride In methanol; water pH=5;	87%
With potassium tert-butylate In methanol at 23 - 60℃;

2,6-di-tert-butyl-4-(4-methoxybenzylidene)-cyclohexa-2,5-dienone (71711-98-3) + ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → C32H44O5

Conditions	Yield
With C51H62N2O2; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at -15℃; for 18h; enantioselective reaction;	86%

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → 3-cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester (1046450-99-0)

Conditions	Yield
Stage #1: ethyl 3-cyclopentyl-3-oxopropionate With [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate In methanol at 20℃; Stage #2: With water; sodium hydrogencarbonate In dichloromethane	43%

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + acetic acid (64-19-7) → 2-amino-1-cyclopentyl-ethanone (89895-04-5)

Conditions	Yield
With sodium nitrite Behandeln des Reaktionsprodukts mit Zink und Acetanhydrid unter Zusatz von Eis und Erhitzen des danach isolierten Reaktionsprodukts mit wss. Salzsaeure;

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + thiourea (17356-08-0) → 6-cyclopentyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Conditions	Yield
With ethanol; sodium ethanolate

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → 5-cyclopentylisoxazol-3-ol (27772-74-3) + 3-cyclopentyl-2H-isoxazol-5-one (29068-27-7)

Conditions	Yield
(i) NH2OH*HCl, aq. NaOH, (ii) aq. HCl; Multistep reaction;

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → 3-cyclopentyl-2H-isoxazol-5-one (29871-87-2)

Conditions	Yield
With hydroxylamine hydrochloride

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + ethyl bromoacetate (105-36-2) → diethyl 2-(cyclopentanecarbonyl)succinate (1057673-87-6)

Conditions	Yield
With sodium In ethanol

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) + 4-methoxybenzoic acid hydrazide (3290-99-1) → 3-Cyclopentyl-3-[(4-methoxy-benzoyl)-hydrazono]-propionic acid ethyl ester

Conditions	Yield
In isopropyl alcohol for 0.5h; Heating;

2,6-dichlorobenzohydroximoyl chloride (6579-27-7) + ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate (1020568-84-6)

Conditions	Yield
With sodium ethanolate In tetrahydrofuran; ethanol at 0 - 20℃;

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → 4-cyclopentyl-4-oxobutanoic acid (3400-90-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na / ethanol 2: aq. HCl View Scheme

ethyl 3-cyclopentyl-3-oxopropionate (24922-00-7) → 3-cyclopentyl-5-methoxy-isoxazole (29871-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH2OH*HCl View Scheme

Upstream product

• 71911-64-3 6-bicyclo<3.1.0>hexan-6-ol 
• 3400-45-1 cyclopentanecarboxylic acid 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 141-78-6 ethyl acetate 
• 6148-64-7 ethyl potassium malonate 
• 105-53-3 diethyl malonate 
• 64-17-5 ethanol 
• 134302-12-8 5-(cyclopentanecarbonyl)2,2-dimethyl-1,3-dioxane-4,6-dione 
• 71911-61-0 6-bicyclo<3.1.0>hexan-6-ol 
• 6004-60-0 1-cyclopentylethanone 
• 105-58-8 Diethyl carbonate 
• 412018-99-6 2-cyclopentanecarbonyl-3-oxo-butyric acid ethyl ester 
• 811467-21-7 3-cyclopentyl-2-diazo-3-hydroxy-propionic acid ethyl ester 

Downstream Products

• 21260-41-3 7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 83688-40-8 7,9-dihydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 1335027-88-7 ethyl 2-(3-chlorobenzyl)-3-cyclopentyl-3-oxopropanoate 
• 199863-89-3 2-amino-4-chloro-6-cyclopentylpyrimidine 
• 1166831-82-8 ethyl 5-cyclopentyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate 
• 199863-76-8 2-amino-6-cyclopentyl-3H-pyrimidin-4-one 
• 3400-90-6 4-oxo-4-cyclopentylbutanoic acid 
• 1020568-84-6 ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate 
• 212200-63-0 ethyl 3-amino-3-cyclopentylacrylate 
• 29871-87-2 3-cyclopentyl-2H-isoxazol-5-one 
• 27772-74-3 5-cyclopentylisoxazol-3-ol 
• 29068-27-7 3-cyclopentyl-2H-isoxazol-5-one 

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