56834-42-5

Basic information

• Product Name: Propanedioic acid, methyl-, 1,1-dimethylethyl ethyl ester
• Synonyms: t-butyl ethyl methylmalonate;tert-butyl ethyl methylmalonate;t-butyl ethyl 2-methylmalonate;tert-butyl ethyl-2-methylmalonate;Propanedioic acid,methyl-,1,1-dimethylethyl ethyl ester;tert-butyl 2-carbethoxypropionate;methyl-malonic acid ethyl ester-tert-butyl ester;Methyl-malonsaeure-aethylester-tert-butylester
• CAS NO: 56834-42-5
• Molecular Formula: C10H18O4
• Molecular Weight: 202.251
• Mol File: 56834-42-5.mol

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, methyl-, 1,1-dimethylethyl ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, methyl-, 1,1-dimethylethyl ethyl ester(56834-42-5)
• EPA Substance Registry System: Propanedioic acid, methyl-, 1,1-dimethylethyl ethyl ester(56834-42-5)

Safety Data

• Hazardous Substances Data: 56834-42-5(Hazardous Substances Data)

Upstream product

• 2985-33-3 monoethyl methylmalonate 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 37472-52-9 α-methylmalonate mono-tert-butyl ester 
• 1196866-19-9 t-butyl ethyl 2-{3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl}-2-methyl-propane dioate 
• 1196866-20-2 C₂₂H₂₁ClF₃N₃O₃S 
• 1006727-21-4 ethyl hydrogen 2-{3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl}-2-methyl-propane dioate 

Relevant articles and documents

Facile acylation of sterically hindered alcohols through ketene intermediates

Figure presented Carboxylic acids possessing strongly electron withdrawing substituents in the α-position in the presence of DCC acylate sterically hindered and chemically sensitive alcohols. The pattern of reactivity, the deuteration experiments, and the formation of a product derived from a [4 + 2] cycloaddition reaction corroborate the existence of ketene intermediates in the reaction.

Acylation through ketene intermediates

Carboxylic acids possessing a strong electron-withdrawing group in the α-position undergo facile dehydration upon reaction with carbodiimides to form the corresponding substituted ketenes that can react in situ with alcohols providing esters in a high yield. The ketene formed by the treatment of ethyl 2-methylmalonate with DCC was trapped in situ by a [4+2] cycloaddition with a second DCC molecule. The chemoselectivity of the acylation through the ketene intermediates was found to be substantially different from that of conventional acylation reagents showing a very low sensitivity toward the steric bulk of alcohols. A comparison of the sensitivity of the acylation to the steric bulk of alcohols supports the presence of a pseudopericyclic pathway for the nucleophilic addition of alcohols to ketenes derived from ethyl malonic and diethylphosphonoacetic acid.

Reaction of lithium trimethylsilyldiazomethanide with ketenimines bearing electron-withdrawing groups

Ketenimines bearing electron-withdrawing groups (X in 1) at the C2-position react with lithium trimethylsilyldiazomethanide [diazo(lithio)trimethylsilylmethane] to give 4-amino-3-trimethylsilylpyrazoles 4 or 5 mainly; in some cases 4-trimethylsilyl-1,2,3-triazole derivatives 3 were formed as the major products.