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62462-05-9

62462-05-9 Structure

62462-05-9 Structure
IdentificationBack Directory
[Name]

5-METHOXY-3-OXOVALERIC ACID METHYL ESTER
[CAS]

62462-05-9
[Synonyms]

NAZAROV REAGENT
METHYL 5-METHOXY-3-OXOALERATE
METHYL 5-METHOXY-3-OXOVALERATE
METHYL 3-KETO-5-METHOXYVALERATE
METHYL 5-METHOXY-3-OXOPENTANOATE
Methyl5-Methoxy-3-oxovalerate>
5-METHOXY-3-OXOVALERIC ACID METHYL ESTER
3-KETO-5-METHOXYVALERIC ACID METHYL ESTER
5-Methoxy-3-oxopentanoic acid methyl ester
M**5-METHOXY-3-OXOVALERIC ACID METHYL ESTER
Pentanoic acid, 5-methoxy-3-oxo-, methyl ester
Methyl 5-methoxy-3-oxopentanoate, Nazarov reagent
3-Keto-5-methoxyvaleric Acid Methyl Ester 5-Methoxy-3-oxovaleric Acid Methyl Ester Methyl 3-Keto-5-methoxyvalerate
[EINECS(EC#)]

263-553-9
[Molecular Formula]

C7H12O4
[MDL Number]

MFCD00042840
[MOL File]

62462-05-9.mol
[Molecular Weight]

160.17
Chemical PropertiesBack Directory
[Boiling point ]

56-57 °C0.1 mm Hg(lit.)
[density ]

1.10 g/mL at 20 °C(lit.)
[refractive index ]

n20/D 1.44
[Fp ]

104 °C
[storage temp. ]

Storage temp. 2-8°C
[form ]

clear liquid
[pka]

10.38±0.46(Predicted)
[color ]

Colorless to Almost colorless
[BRN ]

2042099
[InChI]

1S/C7H12O4/c1-10-4-3-6(8)5-7(9)11-2/h3-5H2,1-2H3
[InChIKey]

OPURNNHYTATPKM-UHFFFAOYSA-N
[SMILES]

COCCC(=O)CC(=O)OC
[LogP]

0.497 (est)
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2918999090
[Storage Class]

10 - Combustible liquids
Hazard InformationBack Directory
[Uses]

5-METHOXY-3-OXOVALERIC ACID METHYL ESTER is used as a precursor to the annulating agent and Nazarov's reagent.[1] It can function as an annulating agent under acidic reaction conditions.[2]
[Synthesis Reference(s)]

Synthesis, p. 622, 1979 DOI: 10.1055/s-1979-28786
[Synthesis]

3-METHOXYPROPIONIC ACID

2544-06-1

Potassium 3-methoxy-3-oxopropanoate

38330-80-2

5-METHOXY-3-OXOVALERIC ACID METHYL ESTER

62462-05-9

1. 3-Methoxypropionic acid (1.81 mL, 19.2 mmol) was suspended in anhydrous acetonitrile (80 mL) and stirred. 2. Methyl 5-methoxy-3-oxopentanoate (3.24 g, 20.0 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 1.5 h. 3. A powdered mixture of magnesium chloride (1.57 g, 16.5 mmol) and potassium methyl malonate (4.5 g, 28.8 mmol) was added in one portion (note that CO2 gas was produced during the reaction). 4. The reaction mixture continued to be stirred at room temperature. 5. MgCl2 (1.57 g, 16.5 mmol) and potassium malonate monohydrate (4.5 g, 28.8 mmol) in a powdered mixture (note that CO2 gas is produced during the reaction). 4. Continue to stir the reaction mixture at room temperature. 5. Vacuum remove the volatiles, then add 2M hydrochloric acid (105 mL). 6. Stir the solution for 1 hour at room temperature, and then extract it with dichloromethane (3 x 100 mL). 7. Combine the organic phases, dry them with MgSO4, filter, and remove the solvents in vacuum. 8. dried, filtered and the solvent was removed in vacuum to afford the target product methyl 5-methoxy-3-oxovalerate (2.69 g, 87% yield).

[References]

[1] Patent: WO2016/83816, 2016, A1. Location in patent: Page/Page column 46
Spectrum DetailBack Directory
[Spectrum Detail]

5-METHOXY-3-OXOVALERIC ACID METHYL ESTER(62462-05-9)MS
5-METHOXY-3-OXOVALERIC ACID METHYL ESTER(62462-05-9)1HNMR
5-METHOXY-3-OXOVALERIC ACID METHYL ESTER(62462-05-9)13CNMR
5-METHOXY-3-OXOVALERIC ACID METHYL ESTER(62462-05-9)IR1
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