163041-49-4

Upstream product

• 4294-57-9 para-methylphenylmagnesium bromide 
• 27579-31-3 methyl (Z)-2-chloro-3-methoxyacrylate 
• 5720-05-8 4-methylphenylboronic acid 
• 90252-89-4 p-tolylzinc(II) chloride 
• 163041-47-2 (Z)-3-methoxy-2-iodo-acrylic acid methyl ester 

Downstream Products

• 262268-42-8 methyl (E)-2-[4-(dimethoxyphosphorylmethyl)phenyl]-3-methoxyacrylate 
• 262268-43-9 (E)-2-(4-Bromomethyl-phenyl)-3-methoxy-acrylic acid methyl ester 

Relevant academic research and scientific papers

Dehydration-type Ti-Claisen Condensation (Carbonhomologation) of α-Heteroatom-substituted Acetates with Alkyl Formates: Utilization as (Z)-Stereodefined Cross-coupling Partners and Application to Concise Synthesis of Strobilurin A

TiCl4?Et3N or ?Bu3N reagent conducted a highly (Z)-stereoselective carbon homologation (dehydration type Ti-Claisen condensation) of alkyl α-heteroatom (halo and sulfonyloxy)-substituted acetates (XCH2CO2R) with alkyl formates (HCO2R) to afford various alkyl β-alkoxy-α-halo or sulfonyloxy-substituted acrylates (24 examples; 51%–91% yield). Stereoretentive Suzuki-Miyaura, Negishi, and Sonogashira cross-couplings using the obtained methyl β-methoxy-α-halo or sulfonyloxy-substituted acrylates proceeded smoothly to produce a variety of β-alkoxy-α-substituted acrylates in moderate to high yield (35 examples; 29%–99% yield). As a successful application, a 3-step straightforward synthesis of strobilurin A was performed utilizing the present reaction sequence (dehydration type Ti-Claisen condensation and Suzuki-Miyaura cross-coupling), wherein the geometry of the three consecutive olefins (2E,3Z,5E) was completely maintained. (Figure presented.).

Preparation process for beta-alkoxy acrylic acid

A method for prerparing compounds of formula (I), wherein R is an optionally substituted alkenyl or alkynyl radical having up to 8 carbon atoms, or an optionally substituted mono- or polycyclic aryl or heteroaryl radical, and R1 and R2/su