6460-86-2

Upstream product

• 101-41-7 benzeneacetic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 163041-47-2 (Z)-3-methoxy-2-iodo-acrylic acid methyl ester 
• 28557-00-8 phenylzinc chloride 
• 27579-31-3 methyl (Z)-2-chloro-3-methoxyacrylate 
• 100-58-3 phenylmagnesium bromide 
• 77-78-1 dimethyl sulfate 
• 149-73-5 trimethyl orthoformate 
• 186581-53-3 diazomethane 
• 6460-85-1 β-Methoxy-α-phenylacrylsaeure 
• 1600-39-1 2-hydroxy-3-phenylcyclopropenone 
• 6460-83-9 2-Methoxy-3-phenylcyclopropenone 

Relevant academic research and scientific papers

Method for synthesis -2- of 3- methyl ester compound (methyl ethyl ester) of methyl ethyl ester (methyl) ethyl ester

The invention relates to a synthesis method of 3-methoxy-2-aryl(methyl)acrylate compounds, which comprises the following steps: by using phenylmethyl acetate with or without substituting groups as a raw material, carrying out formylation reaction at -20-100 DEG C for 4-6 hours in a nitrogen atmosphere in the presence of Lewis acid in an aprotic solvent neutralized formylation reagent, dissociating with an organic base, hydrolyzing with hydrochloric acid, and stratifying, wherein the organic layer is an intermediate; carrying out methylation reaction on the intermediate, benzyltriethylammonium chloride, a methylation reagent and an inorganic base at 20-100 DEG C for 1-3 hours; after the reaction finishes, washing with water, desolventizing, and recrystallizing or distilling while depressurizing to obtain the product. The invention has the advantages of fewer processing steps (the methylation reaction can be directly carried out without purifying and separating the intermediate product), favorable selectivity, higher yield and low cost; and the reaction process is easy to control, and is safe and easy to amplify.

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.).