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261432 Sigma-Aldrich

Methyl coumalate

98%

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

  • CAS Number 6018-41-3

  • Empirical Formula (Hill Notation) C7H6O4

  • Molecular Weight 154.12

  •  Beilstein/REAXYS Number 126301

  •  EC Number 227-871-1

  •  MDL number MFCD00010120

  •  PubChem Substance ID 24855810

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Properties

Related Categories Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, Pyrans
InChI Key   HHWWWZQYHPFCBY-UHFFFAOYSA-N
assay   98%
bp   178-180 °C/60 mmHg(lit.)
mp   65-67 °C (lit.)

Description

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.

Packaging

1, 10 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

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 vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

Peer-Reviewed Papers
15

References

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