184719-42-4

Basic information

• Product Name: 2H-Pyran-5-carboxylicacid,2-ethoxy-3,4-dihydro-4-oxo-,methylester(9CI)
• Synonyms: 2H-Pyran-5-carboxylicacid,2-ethoxy-3,4-dihydro-4-oxo-,methylester(9CI)
• CAS NO: 184719-42-4
• Molecular Formula: C9H12O5
• Molecular Weight: 0
• Product Categories: ETHOXY
• Mol File: 184719-42-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Pyran-5-carboxylicacid,2-ethoxy-3,4-dihydro-4-oxo-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-5-carboxylicacid,2-ethoxy-3,4-dihydro-4-oxo-,methylester(9CI)(184719-42-4)
• EPA Substance Registry System: 2H-Pyran-5-carboxylicacid,2-ethoxy-3,4-dihydro-4-oxo-,methylester(9CI)(184719-42-4)

Safety Data

• Hazardous Substances Data: 184719-42-4(Hazardous Substances Data)

Upstream product

• 64516-46-7 Methyl diformylacetate 

Downstream Products

• 184719-44-6 4-Oxo-4H-pyran-3-carboxylic acid methyl ester 

Relevant articles and documents

A synthetic entry to the trichothecene nucleus via cargill rearrangement. Formal synthesis of (±)-verrucarol

A formal synthesis of (±)-verrucarol (4) was completed via a route which began from 3-carbomethoxy-5-methyl-4-oxo-2H-pyran (22). A Diels-Alder reaction of this pyrone with 2-ethoxybuta-1,3-diene gave the bicyclic adduct 25, and a second annulation employing photoaddition of acetylene led to the cyclobutene 27. The latter underwent an acid-catalyzed Cargill rearrangement to lactone 28 which, after conversion to 34, suffered further rearrangement in the presence of a palladium(0) catalyst to 35. This tetracyclic lactone has previously been converted to (±)-verrucarol by Trost.