83026-48-6

Basic information

• Product Name: diethyl (3-methoxyphenyl)methylpropanedioate
• Synonyms: diethyl (3-methoxyphenyl)methylpropanedioate
• CAS NO: 83026-48-6
• Molecular Weight: 280.321
• Mol File: 83026-48-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: diethyl (3-methoxyphenyl)methylpropanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (3-methoxyphenyl)methylpropanedioate(83026-48-6)
• EPA Substance Registry System: diethyl (3-methoxyphenyl)methylpropanedioate(83026-48-6)

Safety Data

• Hazardous Substances Data: 83026-48-6(Hazardous Substances Data)

Upstream product

• 79421-99-1 tris(3-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 609-08-5 Diethyl methylmalonate 
• 609-09-6 Diethyl ketomalonate 
• 83026-22-6 diethyl (3-methoxyphenyl)tartronate 
• 2398-37-0 3-methoxyphenyl bromide 
• 50874-07-2 2-(3-methoxyphenyl)malonic acid diethyl ester 
• 74-88-4 methyl iodide 
• 83026-36-2 diethyl acetoxy(3-methoxyphenyl)propanedioate 

Downstream Products

• 178681-71-5 methyl (S)-(-)-5-pivaloyloxy-4-(m-methoxyphenyl)-4-methylpentanoate 
• 178681-78-2 (R)-2-(3-Methoxy-phenyl)-2-methyl-pentanedioic acid 1-ethyl ester 5-methyl ester 
• 178681-58-8 (R)-2-(3-Methoxy-phenyl)-2-methyl-pentanedioic acid 1-ethyl ester 
• 178681-67-9 ethyl (S)-(-)-3-methoxymethoxy-2-(m-methoxyphenyl)-2-methylpropionate 
• 178681-82-8 (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-one 
• 178681-69-1 (S)-3-Methoxymethoxy-2-(3-methoxy-phenyl)-2-methyl-propionaldehyde 
• 178681-55-5 ethyl (S)-(-)-3-hydroxy-2-(m-methoxyphenyl)-2-methylpropionate 
• 178681-56-6 (S)-2-(3-Methoxy-phenyl)-2-methyl-3-oxo-propionic acid ethyl ester 
• 178681-68-0 (R)-(-)-3-hydroxy-2-(m-methoxyphenyl)propyl ether 
• 178681-77-1 (S)-3-hydroxy-(m-methoxyphenyl)-2-methylpropionic acid 
• 128524-63-0 (+)-8-O-methylaphanorphine 
• 118964-06-0 (-)-aphanorphine 
• 3146-60-9 2-(3-methoxyphenyl)propanoic acid 
• 178681-54-4 (R)-2-(m-methoxyphenyl)-2-methylmalonic monoester 

Relevant articles and documents

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

Oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles: The enolate chan–evans–lam reaction

Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40°C), Cu(OTf)2mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross-coupling or SNAr protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley-type conditions, are suitable reaction partners.

Ester Enolates from α-Acetoxy Esters. Synthesis of Aryl Malonic and α-Aryl Alkanoic Esters from Aryl Nucleophiles and α-Keto Esters

Ester enolates are generated by reductive α-deacetoxylation of α-acetoxy-α-arylmalonic esters or α-acetoxy-α-arylalkanoic esters with lithium in liquid ammonia or sodium α-(dimethylamino)naphthalenide in hexamethylphosphoramide-benzene.Since the requisite α-acetoxy esters are available from aryl nucleophiles, the reductions provide effective new synthetic routes to arylmalonic esters and α-arylalkanoic esters.For example, 2-(p-isobutylphenyl)propionic acid (ibuprofen, a commercially important nonsteroidal antiinflammatory agent) is obtained in 73percent yield overall from isobutylbenzene.Arenes, aryllithiums, or arylmagnesium halides react with α-keto esters, e.g., diethyl oxomalonate, ethyl pyruvate, methyl phenylglyoxalate, or alkyl glyoxylates, to afford α-hydroxy esters.These are acetylated with acetic anhydride-triethylamine and p-(dimethylamino)pyridine as a catalyst.Reductive α-deoxygenation then allows replacement of the acetoxy group by hydrogen or an alkyl group.