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261432

Sigma-Aldrich

Methyl coumalate

98%

Synonym(s):

Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C7H6O4
CAS Number:
6018-41-3
Molecular Weight:
154.12
Beilstein:
126301
EC Number:
227-871-1
MDL number:
MFCD00010120
UNSPSC Code:
12352100
PubChem Substance ID:
24855810
NACRES:
NA.22

Assay

98%

form

solid

bp

178-180 °C/60 mmHg (lit.)

mp

65-67 °C (lit.)

SMILES string

COC(=O)C1=COC(=O)C=C1

InChI

1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3

InChI key

HHWWWZQYHPFCBY-UHFFFAOYSA-N

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General description

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.

Application

Methyl coumalate 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Diels-Alder reaction of methyl coumalate with 1, 3-dienes.
Imagawa T, et al.
Tetrahedron, 30(14), 2227-2231 (1974)
Quinolizinium Compounds by Cyclization of Pyridones from Methyl Coumalate and ?-Phenylethylamines.
Wiley RH, et al.
Journal of the American Chemical Society, 75(18), 4482-4484 (1953)
Suqing Zheng et al.
Organic letters, 11(17), 3978-3981 (2009-08-13)
A phosphine-catalyzed [4 + 3] annulation of modified allylic carbonates with methyl coumalate was developed. This strategy offered a powerful method for the construction of bicyclo[3.2.2]nonadiene skeleton with high stereoselectivity.
Aromatics from pyrones: para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate.
Kraus GA, et al.
Green Chemistry, 13(10), 2734-2736 (2011)

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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