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6018-41-3 - Methyl coumalate, 98% - Coumalic acid methyl ester - Methyl 2-oxo-2H-pyran-5-carboxylate - B25330 - Alfa Aesar

B25330 Methyl coumalate, 98%

CAS Number
6018-41-3
Synonyms
Coumalic acid methyl ester
Methyl 2-oxo-2H-pyran-5-carboxylate

Size Price ($) Quantity Availability
2g 41.90
10g 153.00
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Methyl coumalate, 98%

MDL
MFCD00010120
EINECS
227-871-1

Chemical Properties

Formula
C7H6O4
Formula Weight
154.12
Melting point
68-72°
Boiling Point
178-180°/60mm
Solubility
Freely soluble in dichloromethane.

Applications

Methyl coumalate is a 2-pyrone and acts as dienophile in Diels-Alder reaction. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts. It has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives.

Notes

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Literature References

Suqing Zheng; Xiyan Lu. Phosphine-catalyzed [4 + 3] annulation for the synthesis of highly functionalized bicyclo[3.2.2]nonadienes. Organic Letters. 2009, 11,(17), 3978-3981.

 

Richard H.Wiley; Newton R.Smith; Louis H.Knabeschuh. Quinolizinium compounds by cyclization of pyridones from methyl coumalate and β-phenylethylamines. J. Am. Chem. Soc. 1953, 75,(18), 4482-4484.

Other References

Merck
14,2557
Harmonized Tariff Code
2932.20
TSCA
No

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