4525-27-3

Usage

InChI:InChI=1/C7H10O4/c1-5(11-6(2)8)4-7(9)10-3/h4H,1-3H3/b5-4-

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 75-36-5 acetyl chloride 
• 108-22-5 Isopropenyl acetate 
• 108-24-7 acetic anhydride 
• 546-89-4 lithium acetate 
• 23326-27-4 Methyl 2-butynoate 
• 64-19-7 acetic acid 
• 107-02-8 acrolein 

Downstream Products

• 4619-66-3 methyl 2-acetylacetoacetate 
• 50652-79-4 (ZE)-3-methyl-2-pentenoate 
• 289-66-7 1,2-dihydropyrane 

Relevant academic research and scientific papers

Stereoselective Addition of Carboxylic Acids to Electron Deficient Acetylenes Catalyzed by the PdMo3S4 Cubane-Type Cluster

The mixed-metal sulfide cubane-type cluster complex 3 (1; tacn = 1,4,7-triazacyclononane) was found to be a highly efficient and selective catalyst for the addition of carboxylic acids to acetylenes with electron-withdrawing groups.The corresponding trans addition products were exclusively obtained in good yields under mild reaction conditions in the presence of a catalytic amount of triethylamine.

Palladium(II)-Catalyzed Three-Component Coupling Reaction Initiated by Acetoxypalladation of Alkynes: An Efficient Route to γ,δ-Unsaturated Carbonyls

(Matrix Presented) A divalent palladium-catalyzed coupling reaction of electron-deficient alkynes and acrolein or MVK (methyl vinyl ketone) was developed. The reaction provides an efficient method to synthesize γ,δ-unsaturated carbonyls. A mechanism involving acetoxypalladation of alkyne, followed by insertion of alkene and protonolysis of the C-Pd bond, is proposed. The protonolysis of the carbon-palladium bond with the assistance of bidentate nitrogen containing ligands is the key step in this tandem reaction.

A novel regio- and stereo-specific hydroacetoxylation reaction of 2-alkynoic acid derivatives

2-Alkynoic acid derivatives were hydroacetoxylated regio- and stereo-specifically by reaction with lithium acetate in HOAc at rt under the catalysis of palladium acetate to afford 3-acetoxy-2(Z)-alkenoic acid derivatives.

Trifluoromethyl Substituted 4-Pyrones via Self-condensation of Trifluoroacetoacetates

When 3-(acetoxy)-4,4,4-trifluoro-2-butenoates 7 and 8 are heated at 100 deg C, in the presence of catalytic amounts of zinc chloride, they undergo self-condensation to yield 2,6-bis(trifluoromethyl)-4-pyrones 1 and 2 respectively.Compounds 1 and 2 were further converted to the corresponding pyridine derivatives 3 and 4 yia ammonolysis.