(R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate

Base Information

• Chemical Name: (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate
• CAS No.: 1313870-27-7
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• Mol file: 1313870-27-7.mol

Synonyms:(R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate

Chemical Property of (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate

There total 22 articles about (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate 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: 85.0%

ethyl acetoacetate (141-97-9) + hydrocinnamic acid chloride (645-45-4) → (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate (1313870-27-7)

Guidance literature:

hydrocinnamic acid chloride; With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C₂₉H₃₂N₃⁽¹⁺⁾*BF₄^(1-); caesium carbonate; In dichloromethane; toluene; for 0.5h; Inert atmosphere; Molecular sieve;

ethyl acetoacetate; In dichloromethane; toluene; at 20 ℃; for 48h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c8cc08578a

Reference yield: 83.0%

ethyl acetoacetate (141-97-9) + 3-phenyl-propenal (104-55-2) → (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate (1313870-27-7)

Guidance literature:

With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C₂₁H₂₂N₃O⁽¹⁺⁾*Cl^(1-); In toluene; at 40 ℃; for 10h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1039/c1cc12778k

Reference yield: 81.0%

Phenylpropargyl aldehyde (2579-22-8) + ethyl acetoacetate (141-97-9) → (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate (1313870-27-7)

Guidance literature:

With C₂₁H₂₂N₃O⁽¹⁺⁾*Cl^(1-); In toluene; at 40 ℃; for 8h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1039/c1cc12778k

upstream raw materials:

Phenylpropargyl aldehyde

ethyl acetoacetate

3-phenyl-propenal

(E)-3-phenylpropenal

Refernces

• 1、 Breugst, Martin,Cao, Jing,Gillard, Rachel,Jahanbakhsh, Azar,Lupton, David W.. "Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants". . p. 11791 - 11796. Retrieved 2020/11/27.
• 2、 Gao, Yaru,Ma, Yafei,Xu, Chen,Li, Lin,Yang, Tianjian,Sima, Guoqing,Fu, Zhenqian,Huang, Wei. "Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions". supporting information. p. 479 - 484. Retrieved 2017/12/26.