(Z)-benzyl methyl (phenylmethylene)malonate

Base Information

• Chemical Name: (Z)-benzyl methyl (phenylmethylene)malonate
• CAS No.: 114995-75-4
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.323
• Mol file: 114995-75-4.mol

Synonyms:(Z)-benzyl methyl (phenylmethylene)malonate

Chemical Property of (Z)-benzyl methyl (phenylmethylene)malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-benzyl methyl (phenylmethylene)malonate

There total 3 articles about (Z)-benzyl methyl (phenylmethylene)malonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

benzyl (E)-3-phenyl-2-(tributylstannyl)acrylate + methyl chloroformate (79-22-1) → (Z)-benzyl methyl (phenylmethylene)malonate (114995-75-4)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In 1,2-dimethoxyethane; at 80 ℃; for 12h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201403429

Reference yield:

benzyl methyl malonate (52267-39-7) + benzaldehyde (100-52-7) → (Z)-benzyl methyl (phenylmethylene)malonate (114995-75-4) + (E)-benzyl methyl (phenylmethylene)malonate (114995-74-3)

Guidance literature:

With piperidine; In benzene; for 12h; Heating;

DOI:10.1021/jo00250a002

Reference yield:

benzyl 3-phenyl-2-propynoate (63888-21-1) → (Z)-benzyl methyl (phenylmethylene)malonate (114995-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2: triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / 1,2-dimethoxyethane / 12 h / 80 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1002/ejoc.201403429

upstream raw materials:

benzyl methyl malonate

benzaldehyde

methyl chloroformate

benzyl 3-phenyl-2-propynoate

Downstream raw materials:

trans-benzyl methyl 2-phenyl-6,10-dioxaspiro<4.5>dec-3-ene-1,1-dicarboxylate

cis-benzyl methyl 2-phenyl-6,10-dioxaspiro<4.5>dec-3-ene-1,1-dicarboxylate

tricyclo(3.1.0.0^2,4)hexane-3,6-dione bis(propane-1,3-diyl) ketal

Refernces

• 1、 Boger, Dale L.,Wysocki, Ronald J.. "Thermal Cycloaddition Reactions of ?-Delocalized Singlet Vinylcarbenes: Three-Carbon 1,1-/1,3-Dipoles. The Thermal Three-Carbon + Two-Carbon Cycloaddition". . p. 3408 - 3421. Retrieved 2007/10/02.