22524-02-3

Basic information

• Product Name: diethyl pivaloylMalonate
• Synonyms: diethyl pivaloylMalonate
• CAS NO: 22524-02-3
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244.2842
• Mol File: 22524-02-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 287.2°Cat760mmHg
• Flash Point: 119.4°C
• Appearance: /
• Density: 1.056g/cm³
• Vapor Pressure: 0.00252mmHg at 25°C
• Refractive Index: 1.441
• CAS DataBase Reference: diethyl pivaloylMalonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl pivaloylMalonate(22524-02-3)
• EPA Substance Registry System: diethyl pivaloylMalonate(22524-02-3)

Safety Data

• Hazardous Substances Data: 22524-02-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H20O5/c1-6-16-10(14)8(11(15)17-7-2)9(13)12(3,4)5/h8H,6-7H2,1-5H3

Upstream product

• 996-82-7 sodium diethylmalonate 
• 77320-47-9 1--2,2-dimethylcyclopropanol 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 3282-30-2 pivaloyl chloride 
• 105-53-3 diethyl malonate 
• 137786-67-5 ethyl 3-amino-2-ethoxycarbonyl-2-butenoate 
• 570-08-1 diethyl acetylmalonate 

Downstream Products

• 17094-34-7 ethyl pivaloylacetate 

Relevant articles and documents

Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4- dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide i

Procedures for the Acylation of Diethyl Malonate and Ethyl Acetoacetate with Acid Chlorides Using Tertiary Amine Bases and Magnesium Chloride

In the presence of magnesium chloride and 2 equiv of triethylamine, diethyl malonate is C-acylated in excellent yields by acid chlorides.A variety of other metal chlorides were ineffective.Similarly, ethyl acetoacetate is C-acylated by acid chlorides in the presence of magnesium chloride and 2 equiv of pyridine.

Malonate Anion Induced Favorskii Type Rearrangement. 21. Reaction of Acyclic α-Halo Ketones with Carbanions Leading to Cyclopropanols2

The reaction of 3-bromo-3-methyl-2-butanone (6a) with ethyl sodiomalonate (2) in refluxing THF gave 1--2,2-dimethylcyclopropanol (9a), the Favorskii-type intermediate, in 51percent yield.Similar reactions of acyclic halo ketones such as 2-bromo-2-methyl-3-pentanone (6b), 1-acetyl-1-bromocyclohexane (6c), and 1-acetyl-1-bromocyclopentane (6d) with 2 also gave the corresponding cyclopropanols 9b-d in 42-56percent yields.On the contrary, the α-halo ketones (6f-l) possessing a primary or secondary carbon atom at the α position afforded the SN2 products10f-l.The behavior of 3-chloro-3-methyl-2-butanone (6e) was quite different from that of its bromo homologue 6a, giving a mixture (16:45:39) of 9a, 1,1-bis-2,2-dimethylcyclopropane (14), and 1--2,2-dimethyl-1-cyclopropane (15) in 75percent total yield.Hydrolysis of 9a with 0.2 N NaOH at room temperature gave the acid ester 18, which afforded a mixture of 3-carboxy-4,5,5-trimethyl-2(5H)-furanone (22a, 27percent yield) and its ethyl ester (22b, 39percent yield) on heating.When the hydrolysis was carried out in 2 N NaOH at 10 deg C, 9a gave 1-(dicarboxymethyl)-2,2-dimethylcyclopropanol (23, 60percent yield) together with 22a (27percent yield).Similar hydrolysis of 9a at 30 deg C afforded 4,4-dimethyl-3-oxopentanoic acid (24, 38percent yield) and 3,3-dimethyl-2-butanone (25, 18percent yield).The bromination of 9a with Br2 caused the ring opening to give ethyl 5-bromo-4,4-dimethyl-2-(ethoxycarbonyl)-3-oxopentanoate (30) in 76percent yield.The ester 30 was cyclized to the oxetane 31 in 77percent yield.