228271-59-8

Basic information

• Product Name: 3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester
• CAS NO: 228271-59-8
• Molecular Weight: 163.176
• Mol File: 228271-59-8.mol

Chemical Properties

• CAS DataBase Reference: 3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester(228271-59-8)
• EPA Substance Registry System: 3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester(228271-59-8)

Safety Data

• Hazardous Substances Data: 228271-59-8(Hazardous Substances Data)

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 59607-98-6 3-(3'-pyridinyl)-(Z)-propenoic acid ethyl ester 
• 59607-99-7 ethyl (E)-3-(pyridin-3-yl)acrylate 
• 155170-47-1 (Z)-3-(pyridin-3-yl)acrylic acid 
• 228271-74-7 (Z)-N-methyl-3-(3-pyridyl)-2-propenylamine 
• 218593-98-7 (Z)-3-(3-pyridyl)-2-propen-1-ol 

Relevant articles and documents

Wittig reactions in water media employing stabilized ylides with aldehydes. Synthesis of α,β-unsaturated esters from mixing aldehydes, α-bromoesters, and Ph3P in aqueous NaHCO3

(Chemical Equation Presented) Water is demonstrated to be an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities (up to 99%) are achieved, and the rate of the reactions in water is unexpectedly accelerated. The efficiency of water as a medium in the Wittig reaction is compared to conventional organic solvents ranging from carbon tetrachloride to methanol. The aqueous Wittig reaction works best when large hydrophobic entities are present, such as aromatic, heterocyclic aromatic carboxaldehydes, and long-chain aliphatic aldehydes with triphenylphosphoranes. The E/Z-isomeric ratio of the Wittig products appears dependent on the electron-accepting/donating capacity and the location of the substituents present in the aromatic ring. The effect of additives, such as benzoic acid, LiCl, and sodium dodecyl sulfate (SDS), on the Wittig reaction has been explored. The Wittig reaction can also be conducted in the presence of acidic entities, such as phenols and carboxylic acids. In addition, large α-substituents in the aliphatic aldehydes do not jeopardize the reaction. It is also demonstrated that hydrates of aldehydes can be used directly in the aqueous Wittig reaction as substrates. The scope of the aqueous Wittig reaction is extended to 24 examples of one-pot mixtures of Ph3P, α-bromoesters, and aldehydes in sodium bicarbonate solution (at 20°C for 40 min to 3 h) to provide Wittig products of up to 99% yield and up to 98% E-selectivity. Since water is inexpensive, extremely easy to handle, and represents no environmental concerns, it should be considered a possible medium for new organic reactions.

Diastereoselective method of preparing olefins by means of the horner-wadsworthemmons reaction, comprising the addition of a tris-(polyoxaalkyl)-amine sequestering agent

The invention relates to a process for the diastereoselective preparation of olefins via the Homer-Wadsworth-Emmons reaction, which consists in reacting at low temperature a phosphonate with a carbonyl derivative in the presence of a base in a suitable solvent, characterized in that a tris(polyoxaalkyl)amine sequestering reagent of formula (I): N—[CHR1—CHR2—O—(CHR3—CHR4—O)n—R5]3 (I), wherein: n is an integer between 0 and 10; R1, R2, R3 and R4 may be identical or different, and represent a hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms; R5 represents a hydrogen atom, an alkyl or cycloalkyl radical containing up to 12 carbon atoms, a phenyl radical or a radical of formula —CμH2μ-Φ, or CmH2m+1-Φ-, with m being an integer between 1 and 12 and Φ being a phenyl radical; is added in an amount that is sufficient to increase the diastereoselectivity of the olefin.