759-67-1

Basic information

• Product Name: Ethyl 2-fluoro-3-oxopentanoate
• Synonyms: 2-FLUORO-3-OXO-PENTANOIC ACID ETHYL ESTER;ETHYL 2-FLUORO-3-OXOPENTANOATE;Ethyl2-fluoro-3-oxovalerate;ETHYL2-FLUORO-3-OXOPENTANOA;6-AMino-hexan-l-ol
• CAS NO: 759-67-1
• Molecular Formula: C₇H₁₁FO₃
• Molecular Weight: 162.16
• EINECS: 1592732-453-0
• Mol File: 759-67-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 191.7 °C at 760 mmHg
• Flash Point: 68.2 °C
• Appearance: /
• Density: 1.077 g/cm³
• Refractive Index: 1.398
• PKA: 9.14±0.46(Predicted)
• CAS DataBase Reference: Ethyl 2-fluoro-3-oxopentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-fluoro-3-oxopentanoate(759-67-1)
• EPA Substance Registry System: Ethyl 2-fluoro-3-oxopentanoate(759-67-1)

Safety Data

• Hazardous Substances Data: 759-67-1(Hazardous Substances Data)

Usage

Uses

Ethyl 2-fluoro-3-oxopentanoate belongs to ester organic compounds and can be used as pharmaceutical intermediates.

InChI:InChI=1/C7H11FO3/c1-3-5(9)6(8)7(10)11-4-2/h6H,3-4H2,1-2H3

Synthetic route

2-fluoro-3-oxopentanoic acid-O3,O4-diacetic acid borate + propionyl chloride (79-03-8) → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
Reflux;	94.6%

ethyl propanoylacetate (4949-44-4) → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
With Selectfluor In acetonitrile at 50℃; Inert atmosphere;	86%

ethyl 2-fluoroacetate (459-72-3) + propionyl chloride (79-03-8) → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
With sodium ethanolate; triethylamine In tetrahydrofuran at 15℃; for 16h; Solvent; Time; Temperature; Reagent/catalyst;	85%
With sodium ethanolate; triethylamine In tetrachloromethane at 5 - 25℃; for 16h;

ethyl-2-fluoroacetoacetate (1522-41-4) + methyl iodide (74-88-4) → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
Stage #1: ethyl-2-fluoroacetoacetate With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 14h;	59%

ethyl 2-fluoroacetate (459-72-3) → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
With diethyl ether; sodium hydride Erwaermen des Reaktionsgemisches mit Propionylchlorid;

ethyl bromofluoroacetate (401-55-8) + propionyl chloride (79-03-8) → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
Yield given. Multistep reaction;

Tributyl-(1-ethoxycarbonyl-1-fluoro-2-oxo-butyl)-phosphonium; chloride → 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water for 6h; Ambient temperature; Yield given;

ethyl 3-hydroxypent-4-enoate (38996-01-9) → ethyl α-fluoropropionylacetate (227184-02-3) + 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + C7H10F2O3 (1340481-55-1) + ethyl propanoylacetate (4949-44-4)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Selectfluor In tetrahydrofuran; water regiospecific reaction;

4-penten-3-one (1629-58-9) + 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → 2-Fluoro-5-oxo-2-propionyl-heptanoic acid ethyl ester (102283-25-0)

Conditions	Yield
With potassium fluoride In sulfolane for 2h; Ambient temperature;	92%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + methyl vinyl ketone (78-94-4) → 2-Fluoro-5-oxo-2-propionyl-hexanoic acid ethyl ester (102283-24-9)

Conditions	Yield
With potassium fluoride In sulfolane for 2h; Ambient temperature;	89%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + di-tert-butyl-diazodicarboxylate (870-50-8) → C17H29FN2O7 (1179476-79-9)

Conditions	Yield
Stage #1: 2-fluoro-3-oxopentanoic acid ethyl ester With C40H48Br2F4N4Ni In toluene at 20℃; for 0.166667h; Stage #2: di-tert-butyl-diazodicarboxylate In toluene at 20℃; for 20h; enantioselective reaction;	85%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + 2-azidobenzaldehyde (16714-25-3) → ethyl 2-ethyl-4-hydroxyquinoline-3-carboxylate (86540-36-5)

Conditions	Yield
With triethylamine; triphenylphosphine In acetonitrile at 95℃; for 12h; Knoevenagel Condensation;	83%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + (E)-1-([1,1'-biphenyl]-2-yl)but-2-en-1-one → 2,5-dimethyl-[1,1':2',1''-terphenyl]-3-ol

Conditions	Yield
With caesium carbonate In acetonitrile at 125℃; for 5h;	83%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + tert-butyl 5-methylene-2-oxo-1,3-oxazinane-3-carboxylate → ethyl 4-({[(tert-butoxy)carbonyl]amino}methyl)-2-fluoro-2-propanoylpent-4-enoate

Conditions	Yield
Stage #1: tert-butyl 5-methylene-2-oxo-1,3-oxazinane-3-carboxylate With O,O'-(1,1'-biphenyl-2,2'-diyl)-N,N'-diisopropylphosphoramidite; bis(dibenzylideneacetone)-palladium(0) In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Sealed tube; Stage #2: 2-fluoro-3-oxopentanoic acid ethyl ester In dichloromethane at 20℃; for 18h; Inert atmosphere; Sealed tube;	83%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + (E)-1-(2-methoxyphenyl)but-2-en-1-one (40872-81-9) → 2'-methoxy-2,5-dimethyl-[1,1'-biphenyl]-3-ol

Conditions	Yield
With caesium carbonate In acetonitrile at 125℃; for 5h;	76%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + 2,6-dimethoxy-4-methylphenol (6638-05-7) → ethyl 2-fluoro-2-(4-hydroxy-3,5-dimethoxybenzyl)-3-oxopentanoate

Conditions	Yield
With copper diacetate In acetonitrile at 70℃; for 2.5h;	73%

(E)-1-(naphthalen-1-yl)but-2-en-1-one (128113-46-2) + 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → 2,5-dimethyl-3-(naphthalen-1-yl)phenol

Conditions	Yield
With caesium carbonate In acetonitrile at 125℃; for 5h;	72%

chloro-trimethyl-silane (75-77-4) + 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → C10H19FO3Si (1257084-53-9)

Conditions	Yield
With triethylamine In benzene at 20℃; for 48h;	67%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + urea (57-13-6) → C6H7FN2O2

Conditions	Yield
Stage #1: urea With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: 2-fluoro-3-oxopentanoic acid ethyl ester In methanol for 2.5h; Reflux;	66.42%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + (E)-1-(2-chlorophenyl)but-2-en-1-one (1313028-19-1) → 2'-chloro-2,5-dimethyl-[1,1'-biphenyl]-3-ol

Conditions	Yield
With caesium carbonate In acetonitrile at 125℃; for 5h;	63%

(E)-1-(o-tolyl)but-2-en-1-one + 2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → 2,2',5-trimethyl-[1,1'-biphenyl]-3-ol

Conditions	Yield
With caesium carbonate In acetonitrile at 125℃; for 5h;	56%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + (E)-1-(2-(trifluoromethyl)phenyl)but-2-en-1-one (1360924-07-7) → 2,5-dimethyl-2'-(trifluoromethyl)-[1,1'-biphenyl]-3-ol

Conditions	Yield
With caesium carbonate In acetonitrile at 125℃; for 5h;	33%

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + guanidine hydrochloride (50-01-1) → 6-ethyl-2-amino-5-fluoro-3H-pyrimidin-4-one (700-54-9)

Conditions	Yield
With methanol; sodium methylate

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) + formamidine acetic acid (3473-63-0) → 6-Ethyl-5-fluoropyrimidin-4(3H)-one (137234-87-8)

Conditions	Yield
With methanol; sodium methylate Multistep reaction;

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → 4-chloro-5-fluoro-6-ethylpyrimidine (137234-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating View Scheme
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 20 h / 15 °C 2: trichlorophosphate / 3 h / 60 °C View Scheme

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating 3: LDA / tetrahydrofuran 4: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → voriconazole (137234-62-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating 3: LDA / tetrahydrofuran 4: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating 3: LDA / tetrahydrofuran View Scheme

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → (2S,3S)-3-(6-Chloro-5-fluoro-pyrimidin-4-yl)-2-(2,4-difluoro-phenyl)-1-[1,2,4]triazol-1-yl-butan-2-ol

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating 3: LDA / tetrahydrofuran View Scheme

2-fluoro-3-oxopentanoic acid ethyl ester (759-67-1) → C7H12FNO2

Conditions	Yield
With ammonia In formamide for 1h;

Upstream product

• 1522-41-4 ethyl-2-fluoroacetoacetate 
• 74-88-4 methyl iodide 
• 459-72-3 ethyl 2-fluoroacetate 
• 79-03-8 propionyl chloride 
• 4949-44-4 ethyl propanoylacetate 
• 38996-01-9 ethyl 3-hydroxypent-4-enoate 
• 401-55-8 ethyl bromofluoroacetate 

Downstream Products

• 700-54-9 6-ethyl-2-amino-5-fluoro-3H-pyrimidin-4-one 
• 137234-87-8 6-Ethyl-5-fluoropyrimidin-4(3H)-one 
• 188416-28-6 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane 
• 137234-87-8 6-ethyl-5-fluoro-4-hydroxypyrimidine 
• 137234-62-9 voriconazole 
• 137234-63-0 (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 137234-74-3 4-chloro-6-ethyl-5-fluoropyrimidine 

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